Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate supplier

Name
Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate
EINECS 808-698-6
CAS No. 106685-41-0
Article Data16
CAS DataBase
Density 1.186 g/cm³
Solubility
Melting Point 223-225°C
Formula C₂₉H₃₀O₃
Boiling Point 589.632 °C at 760 mmHg
Molecular Weight 426.555
Flash Point 258.722 °C
Transport Information
Appearance white to off white crystal
Safety 26
Risk Codes 36/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Naphthalenecarboxylicacid, 6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-, methyl ester;
PSA 35.53000
LogP 6.76980

Synthetic route

: 459423-32-6
3-(1-adamantyl)-4-methoxyphenylboronic acid

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	92%
Suzuki-Miyaura coupling;

: 459423-32-6
3-(1-adamantyl)-4-methoxyphenylboronic acid

: 366799-67-9
2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: tris(3-hydroxypropyl)phosphine; nickel dichloride In tetrahydrofuran for 1h; Heating / reflux; Stage #2: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene With water; potassium carbonate In tetrahydrofuran at 50℃; for 24h; Product distribution / selectivity; Heating / reflux;	90%
Stage #1: tris(3-hydroxypropyl)phosphine; nickel dichloride In tetrahydrofuran for 1h; Heating / reflux; Stage #2: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene With potassium phosphate; water In tetrahydrofuran at 50℃; for 24h; Product distribution / selectivity; Heating / reflux;	82%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine In tetrahydrofuran for 24h; Product distribution / selectivity; Heating / reflux;	78%

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 104224-63-7
2-(1-adamantyl)-4-bromoanisole

A: 932033-57-3
3,3'-diadamantyl-4,4'-dimethoxybiphenyl

B: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2-(1-adamantyl)-4-bromoanisole With magnesium; ethylene dibromide In tetrahydrofuran at 45 - 55℃; for 1.5h; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20 - 25℃; for 1h; Stage #3: methyl 6-bromo-2-naphthoate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20℃; for 2h;	A n/a B 88.83%

...Expand

: 1036766-56-9
2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	87%
With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura coupling; Inert atmosphere;	85%

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 104224-63-7
2-(1-adamantyl)-4-bromoanisole

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2-(1-adamantyl)-4-bromoanisole With iodine; magnesium In tetrahydrofuran at 40℃; for 1h; Inert atmosphere; Stage #2: methyl 6-bromo-2-naphthoate With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride In tetrahydrofuran at 55℃; for 0.75h; Negishi Coupling;	86%
Stage #1: 2-(1-adamantyl)-4-bromoanisole With magnesium; ethylene dibromide In tetrahydrofuran at 20 - 40℃; for 0.5h; Heating / reflux; Stage #2: With zinc(II) chloride In tetrahydrofuran for 1.25h; Heating / reflux; Stage #3: methyl 6-bromo-2-naphthoate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran for 2.16667h;	50%
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; iodine; magnesium; zinc(II) chloride Yield given. Multistep reaction;

: 1036766-57-0
C19H25BO3

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	86%

: 1036766-54-7
3-(1-adamantyl)-4-methoxybenzene magnesium bromide

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride at 55℃; for 0.75h; Negishi coupling reaction;	86%

: 5042-98-8
methyl 6-iodonaphthalene-2-carboxylate

: lithium [3-(1-adamantyl)-4-methoxyphenyl]trimethoxyborate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
for 21h; Suzuki-Miyaura Coupling; Flow reactor;	86%

: 2-(4’-methoxyphenyl)naphthalene-6-methyl ester

: 768-95-6
1-adamanthanol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid In chloroform at 20℃; Solvent;	83%

: 106685-43-2
6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 74-88-4
methyl iodide

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1.5h;	82%

: 106685-40-9
adapalene

: 18107-18-1
diazomethyl-trimethyl-silane

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 0 - 20℃; for 1h;	79%

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C View Scheme

: 106-41-2
4-bromo-phenol

p-bromo-anisole (?): p-bromo-anisole (?)

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane View Scheme

: 768-95-6
1-adamanthanol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h View Scheme

: 104224-68-2
2-(1-adamantyl)-4-bromophenol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 2: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 8 h / Reflux 2: magnesium / tetrahydrofuran / 1 h / 40 °C 3: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 2.2: 1.25 h / Heating / reflux 2.3: 2.17 h View Scheme

Conditions

Conditions	Yield
With sulfuric acid In ethanol; cyclohexane; nitrogen

Conditions

Conditions	Yield
Stage #1: 6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1.5h;

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate In water at 80℃; for 4h; Inert atmosphere;

: 106-41-2
4-bromo-phenol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h View Scheme

: 104224-63-7
2-(1-adamantyl)-4-bromoanisole

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / 1 h / 40 °C 2: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1: n-butyllithium 2: 21 h / Flow reactor View Scheme

: 106685-40-9
adapalene

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 80 °C 2: potassium carbonate / ethyl acetate; water / 4 h / 0 - 20 °C View Scheme

: 106685-64-7
6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoic acid chloride

: 593-56-6
N-methoxylamine hydrochloride

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 0 - 20℃; for 4h;

: 2-methoxycarbonyl-6-naphthol p-toluenesulfonate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C View Scheme

: 5720-07-0
4-methoxyphenylboronic acid

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C View Scheme

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoic acid potassium salt

Conditions

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In methanol; toluene for 3h; Heating / reflux;	99.18%
With potassium hydroxide; water In tetrahydrofuran; 1,4-dioxane at 90℃; for 6h; Product distribution / selectivity; Heating / reflux;	94%
With potassium hydroxide; water In 1,4-dioxane for 2.25 - 4.25h; Product distribution / selectivity; Heating / reflux;

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide Stage #2: With hydrogenchloride In water Product distribution / selectivity;	97%
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide Stage #2: With hydrogenchloride In water Product distribution / selectivity;	96%
With water; sodium hydroxide In propylene glycol	89%

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid sodium salt

Conditions

Conditions	Yield
With sodium hydroxide; water In tetrahydrofuran for 6h; Heating / reflux;	94%
With sodium hydroxide; water In tetrahydrofuran; 1,4-dioxane at 90℃; for 6h; Heating / reflux;	94%

: 459423-32-6
3-(1-adamantyl)-4-methoxyphenylboronic acid

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	92%
Suzuki-Miyaura coupling;

: 459423-32-6
3-(1-adamantyl)-4-methoxyphenylboronic acid

: 366799-67-9
2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: tris(3-hydroxypropyl)phosphine; nickel dichloride In tetrahydrofuran for 1h; Heating / reflux; Stage #2: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene With water; potassium carbonate In tetrahydrofuran at 50℃; for 24h; Product distribution / selectivity; Heating / reflux;	90%
Stage #1: tris(3-hydroxypropyl)phosphine; nickel dichloride In tetrahydrofuran for 1h; Heating / reflux; Stage #2: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 2-methoxycarbonyl-6-(p-tolylsulfonyl)naphthalene With potassium phosphate; water In tetrahydrofuran at 50℃; for 24h; Product distribution / selectivity; Heating / reflux;	82%
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; tricyclohexylphosphine In tetrahydrofuran for 24h; Product distribution / selectivity; Heating / reflux;	78%

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 104224-63-7
2-(1-adamantyl)-4-bromoanisole

A: 932033-57-3
3,3'-diadamantyl-4,4'-dimethoxybiphenyl

B: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2-(1-adamantyl)-4-bromoanisole With magnesium; ethylene dibromide In tetrahydrofuran at 45 - 55℃; for 1.5h; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20 - 25℃; for 1h; Stage #3: methyl 6-bromo-2-naphthoate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20℃; for 2h;	A n/a B 88.83%

...Expand

: 1036766-56-9
2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium phosphate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	87%
With sodium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura coupling; Inert atmosphere;	85%

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 104224-63-7
2-(1-adamantyl)-4-bromoanisole

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 2-(1-adamantyl)-4-bromoanisole With iodine; magnesium In tetrahydrofuran at 40℃; for 1h; Inert atmosphere; Stage #2: methyl 6-bromo-2-naphthoate With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride In tetrahydrofuran at 55℃; for 0.75h; Negishi Coupling;	86%
Stage #1: 2-(1-adamantyl)-4-bromoanisole With magnesium; ethylene dibromide In tetrahydrofuran at 20 - 40℃; for 0.5h; Heating / reflux; Stage #2: With zinc(II) chloride In tetrahydrofuran for 1.25h; Heating / reflux; Stage #3: methyl 6-bromo-2-naphthoate; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran for 2.16667h;	50%
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; iodine; magnesium; zinc(II) chloride Yield given. Multistep reaction;

: 1036766-57-0
C19H25BO3

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran; water Product distribution / selectivity; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	86%

: 1036766-54-7
3-(1-adamantyl)-4-methoxybenzene magnesium bromide

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride at 55℃; for 0.75h; Negishi coupling reaction;	86%

: 5042-98-8
methyl 6-iodonaphthalene-2-carboxylate

: lithium [3-(1-adamantyl)-4-methoxyphenyl]trimethoxyborate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
for 21h; Suzuki-Miyaura Coupling; Flow reactor;	86%

: 2-(4’-methoxyphenyl)naphthalene-6-methyl ester

: 768-95-6
1-adamanthanol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid In chloroform at 20℃; Solvent;	83%

: 106685-43-2
6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 74-88-4
methyl iodide

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1.5h;	82%

: 106685-40-9
adapalene

: 18107-18-1
diazomethyl-trimethyl-silane

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 0 - 20℃; for 1h;	79%

: 33626-98-1
methyl 6-bromo-2-naphthoate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C View Scheme

: 106-41-2
4-bromo-phenol

p-bromo-anisole (?): p-bromo-anisole (?)

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane View Scheme

: 768-95-6
1-adamanthanol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h View Scheme

: 104224-68-2
2-(1-adamantyl)-4-bromophenol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 2: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 8 h / Reflux 2: magnesium / tetrahydrofuran / 1 h / 40 °C 3: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 2.2: 1.25 h / Heating / reflux 2.3: 2.17 h View Scheme

: 2-(4’-methoxyphenyl)naphthalene-6-methyl ester

: 22635-62-7
1-acetyloxyadamantane

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid In ethanol; cyclohexane; nitrogen

: 74-88-4
methyl iodide

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 1.5h;

: 1036766-56-9
2-(3-adamantan-1-yl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

: 93353-66-3
methyl 6-bromonaphthalene-1-carboxylate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate In water at 80℃; for 4h; Inert atmosphere;

: 106-41-2
4-bromo-phenol

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h View Scheme

: 104224-63-7
2-(1-adamantyl)-4-bromoanisole

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium / tetrahydrofuran / 1 h / 40 °C 2: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C View Scheme
Multi-step reaction with 2 steps 1: n-butyllithium 2: 21 h / Flow reactor View Scheme

: 106685-40-9
adapalene

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 4 h / 80 °C 2: potassium carbonate / ethyl acetate; water / 4 h / 0 - 20 °C View Scheme

: 106685-64-7
6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoic acid chloride

: 593-56-6
N-methoxylamine hydrochloride

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 0 - 20℃; for 4h;

: 2-methoxycarbonyl-6-naphthol p-toluenesulfonate

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C View Scheme

: 5720-07-0
4-methoxyphenylboronic acid

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C View Scheme

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoic acid potassium salt

Conditions

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide In methanol; toluene for 3h; Heating / reflux;	99.18%
With potassium hydroxide; water In tetrahydrofuran; 1,4-dioxane at 90℃; for 6h; Product distribution / selectivity; Heating / reflux;	94%
With potassium hydroxide; water In 1,4-dioxane for 2.25 - 4.25h; Product distribution / selectivity; Heating / reflux;

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 106685-40-9
adapalene

Conditions

Conditions	Yield
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide Stage #2: With hydrogenchloride In water Product distribution / selectivity;	97%
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide Stage #2: With hydrogenchloride In water Product distribution / selectivity;	96%
With water; sodium hydroxide In propylene glycol	89%

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid sodium salt

Conditions

Conditions	Yield
With sodium hydroxide; water In tetrahydrofuran for 6h; Heating / reflux;	94%
With sodium hydroxide; water In tetrahydrofuran; 1,4-dioxane at 90℃; for 6h; Heating / reflux;	94%

: C22H22N4O7

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: C50H49N5O9

Conditions

Conditions	Yield
With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In 1,2-dichloro-ethane at 140℃; for 18h; Inert atmosphere;	54%

: 140-29-4
phenylacetonitrile

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: (3r,5r,7r)-1-(2-methoxy-5-(6-((E)-styryl)naphthalen-2-yl)phenyl)adamantane

Conditions

Conditions	Yield
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With lithium aluminium tetrahydride Stage #2: phenylacetonitrile	40%

: 106685-41-0
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester

: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid hydroxyamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol / 8 h / Reflux 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; hydroxylamine hydrochloride / 20 °C / Inert atmosphere View Scheme

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate Chemical Properties

IUPAC Name:Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate
Molecular Formula:C₂₉H₃₀O₃
Molecular Weight:426.55
Appearance:White to offwhite Crystal
Solubility:Microsolubility In THF
Synonyms of Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoate(106685-41-0):
METHYL 6-[3-(1-ADAMANTYL)-4-METHOXYPHENYL]-2-NAPHTHOATE;Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate;Mehtyl 6-[3-(1-adamantyl)-4-methoxy phenyl]-2-naphthoate;6-[3-(1-Adamantyl-4-methoxyphenyl]-2-naphthatemethylester;Methyl6-[3-(1-adamanty)-4-methoxyphenyl]-2-naphthoate;Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate(Adapalene);METYL 6-[3-(1-ADAMANTYL)-4-METHOXY PHENYL]-2-NAPHTHOATE;Mehtyl 6-[3-(1-adamanty)-4-methoxy
Categories of Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoate(106685-41-0):
APIs Intermediate;ADAPALENE;(intermediate of adapalene)

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate Uses

Methyl 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoate(106685-41-0) is used for the synthesis of adapalene.

Product Name

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate

Synthetic route

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate Chemical Properties

Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate Uses

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