Ethyl 3,4-bis(2-methoxyethoxy)benzoate supplier

Name
Ethyl 3,4-bis(2-methoxyethoxy)benzoate
EINECS 605-991-9
CAS No. 183322-16-9
Article Data22
CAS DataBase
Density 1.102 g/cm³
Solubility
Melting Point 55-58 °C
Formula C₁₅H₂₂O₆
Boiling Point 401.7 °C at 760 mmHg
Molecular Weight 298.336
Flash Point 175.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3,4-Bis(2-methoxyethoxy)benzoic acid ethyl ester;
PSA 63.22000
LogP 1.91370

Synthetic route

: 3943-89-3
Ethyl protocatechuate

: 6482-24-2
2-Bromoethyl methyl ether

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 60℃; for 19h; Inert atmosphere;	100%
With potassium carbonate In acetone at 20 - 70℃; for 24h;	93%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 64h; Inert atmosphere; Reflux;	93%

: 819813-71-3
3,4-bis(2-methoxyethoxy)-benzoic acid

: 64-17-5
ethanol

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid Cooling with ice; Reflux;	98%

: 627-42-9
2-chloroethyl methyl ether

: 3943-89-3
Ethyl protocatechuate

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
With 4-(Methylamino)pyridine; potassium carbonate at 90 - 95℃; Temperature; Reagent/catalyst;	95%
With carbon dioxide; ammonia at 50℃; for 0.5h; Temperature; Reagent/catalyst;	94.6%
With potassium tert-butylate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 12h;	87%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone for 120h; Heating;
With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 9h;	95 %Chromat.

: 16427-44-4
2-methoxyethyl methanesulfonate

: 3943-89-3
Ethyl protocatechuate

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In toluene for 6h; Reflux;	95%
With potassium tert-butylate; tetrabutylammomium bromide In N,N-dimethyl-formamide at 30 - 40℃; for 10h;	90.5%

: 3943-89-3
Ethyl protocatechuate

: 17178-10-8
2-methoxy-ethyl p-toluenesulfonyloxy ester

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Reflux;	89%
With potassium carbonate In acetonitrile for 6h; Reflux;	89%

: 4-chloro-6,7-di-(2-methoxyethoxy)quinazoline hydrochloride

: 3943-89-3
Ethyl protocatechuate

: 6482-24-2
2-Bromoethyl methyl ether

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone

...Expand

: 99-50-3
3,4-Dihydroxybenzoic acid

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 10 h / 40 - 80 °C 2: potassium tert-butylate; potassium iodide / N,N-dimethyl-formamide / 12 h / 100 °C View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 179688-26-7
2-nitro-4,5-bis(2-methoxyethoxy)benzoic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid; nitric acid In acetic acid at 20 - 70℃; for 2h;	100%
With sulfuric acid; nitric acid In acetic acid at 15 - 35℃;	100%
With sulfuric acid; nitric acid; acetic anhydride; acetic acid at 40℃; for 2h; Concentration; Large scale;	98.3%

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: C15H22O7

Conditions

Conditions	Yield
Stage #1: 3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester In tetrahydrofuran for 0.5h; Reflux; Stage #2: With peracetic acid; dinitrogen monoxide In tetrahydrofuran at 50℃; under 22502.3 Torr; for 2h; Reagent/catalyst; Temperature; Autoclave;	95.2%

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 819813-71-3
3,4-bis(2-methoxyethoxy)-benzoic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃; for 3h;	90%

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 179688-29-0
6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; nitric acid / 24 h / 20 °C 2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 3: 84 percent / 12 h / 165 - 170 °C View Scheme
Multi-step reaction with 3 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: 94 percent / hydrogen / palladium on activated carbon / methanol 3: 62 percent / formamide / 3 h / 160 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid; nitric acid / 0 °C 2: hydrogen; palladium on activated charcoal / methanol 3: 165 - 170 °C View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 183322-18-1
4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; nitric acid / 24 h / 20 °C 2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 3: 84 percent / 12 h / 165 - 170 °C 4: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C View Scheme
Multi-step reaction with 4 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: 94 percent / hydrogen / palladium on activated carbon / methanol 3: 62 percent / formamide / 3 h / 160 °C 4: 98 percent / oxalyl chloride / CHCl3; dimethylformamide / 1.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 183319-69-9
erlotinib hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic acid; nitric acid / 24 h / 20 °C 2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr 3: 84 percent / 12 h / 165 - 170 °C 4: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C 5: pyridine / propan-2-ol View Scheme
Multi-step reaction with 6 steps 1.1: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness 2.1: palladium 10% on activated carbon / ethanol / 10 h / 20 °C 2.2: 20 °C 3.1: ammonium formate; triethylamine / 6 h / 160 °C 4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 50 °C 5.1: methanol / 3 h / 20 - 30 °C 5.2: 3 h / 50 °C 6.1: hydrogenchloride / water; dichloromethane; methanol / 3 h / 25 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: acetic acid; nitric acid / 24 h / 20 °C
2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr
3: 84 percent / 12 h / 165 - 170 °C
4: phosphoryl choride; N,N-diethylaniline / 0.67 h / 70 - 90 °C
5: pyridine / propan-2-ol
View Scheme

Multi-step reaction with 6 steps
1.1: sulfuric acid; nitric acid / 1 h / 20 °C / Darkness
2.1: palladium 10% on activated carbon / ethanol / 10 h / 20 °C
2.2: 20 °C
3.1: ammonium formate; triethylamine / 6 h / 160 °C
4.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 50 °C
5.1: methanol / 3 h / 20 - 30 °C
5.2: 3 h / 50 °C
6.1: hydrogenchloride / water; dichloromethane; methanol / 3 h / 25 °C
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 179688-27-8
ethyl 2-amino-4,5-bis(2-methoxyethoxy)-benzoate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; nitric acid / 24 h / 20 °C 2: hydrogen / PtO2*H2O / methanol / 20 °C / 2585.74 Torr View Scheme
Multi-step reaction with 2 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: 94 percent / hydrogen / palladium on activated carbon / methanol View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / acetic acid / 15 - 35 °C 2: hydrogen; platinum on carbon / methanol / 20 - 40 °C / 760.05 Torr View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 4-(3'-chloro-4'-fluoroanilino)-6,7-bis(2-methoxyethoxy)-quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: nitric acid; trifluoroacetic acid / CH2Cl2 / 20 °C 2: 94 percent / hydrogen / palladium on activated carbon / methanol 3: 62 percent / formamide / 3 h / 160 °C 4: 98 percent / oxalyl chloride / CHCl3; dimethylformamide / 1.5 h / Heating 5: 53 percent / pyridine / propan-2-ol / 2 h / Heating View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 179688-29-0
6,7-bis(2-methoxyethoxy)quinazolin-4(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid; nitric acid / acetic acid / 15 - 35 °C 2.1: hydrogen; platinum on carbon / methanol / 20 - 40 °C / 760.05 Torr 3.1: N,N-dimethyl-formamide / 10 h / 130 - 140 °C 3.2: 65 - 80 °C View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347720-71-1
9-chloro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: isopropyl alcohol / 4 h / Reflux 5.1: trichlorophosphate / 2 h / Reflux 5.2: pH 10 View Scheme
Multi-step reaction with 5 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: isopropyl alcohol / 4 h / Reflux 5: trichlorophosphate / 2 h / Reflux View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347720-74-4
9-bromo-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: pyridine / acetonitrile / 4 h / Reflux 5.1: trichlorophosphate / 2 h / Reflux 5.2: pH 9 View Scheme
Multi-step reaction with 5 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: pyridine / acetonitrile / 4 h / Reflux 5: trichlorophosphate / 2 h / Reflux View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347719-30-5
9-fluoro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: hydrogenchloride / isopropyl alcohol; water 5.1: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / cooling with ice View Scheme
Multi-step reaction with 5 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: hydrogenchloride / isopropyl alcohol; water / 20 °C 5: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / Cooling with ice View Scheme

Yield

Multi-step reaction with 5 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / isopropyl alcohol; water
5.1: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / cooling with ice
View Scheme

Multi-step reaction with 5 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: hydrogenchloride / isopropyl alcohol; water / 20 °C
5: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / Cooling with ice
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347720-79-9
9-ethynyl-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: pyridine / acetonitrile / 4 h / Reflux 5.1: trichlorophosphate / 2 h / Reflux 5.2: pH 9 6.1: hydrogenchloride / ethanol; water / Heating 7.1: triethylamine / triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux 8.1: sodium hydroxide / toluene / 6 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 8 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: pyridine / acetonitrile / 4 h / Reflux 5: trichlorophosphate / 2 h / Reflux 6: hydrogenchloride / ethanol / Heating 7: triethylamine; triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux 8: sodium hydroxide / toluene / 4 h / Resolution of racemate; Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 9
6.1: hydrogenchloride / ethanol; water / Heating
7.1: triethylamine / triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux
8.1: sodium hydroxide / toluene / 6 h / Inert atmosphere; Reflux
View Scheme

Multi-step reaction with 8 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: pyridine / acetonitrile / 4 h / Reflux
5: trichlorophosphate / 2 h / Reflux
6: hydrogenchloride / ethanol / Heating
7: triethylamine; triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux
8: sodium hydroxide / toluene / 4 h / Resolution of racemate; Inert atmosphere
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347719-34-9
9-nitro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C 5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice View Scheme
Multi-step reaction with 5 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: hydrogenchloride / water; 1,4-dioxane / 7 h / 20 °C 5: triethylamine; methanesulfonyl chloride / chloroform / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C
5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice
View Scheme

Multi-step reaction with 5 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: hydrogenchloride / water; 1,4-dioxane / 7 h / 20 °C
5: triethylamine; methanesulfonyl chloride / chloroform / 20 °C
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347720-84-6
9-amino-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C 5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice 6.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux View Scheme
Multi-step reaction with 6 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: hydrogenchloride / water; 1,4-dioxane / 7 h / 20 °C 5: triethylamine; methanesulfonyl chloride / chloroform / 20 °C 6: hydrogen; palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C
5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice
6.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux
View Scheme

Multi-step reaction with 6 steps
1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice
2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
4: hydrogenchloride / water; 1,4-dioxane / 7 h / 20 °C
5: triethylamine; methanesulfonyl chloride / chloroform / 20 °C
6: hydrogen; palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 9-chloro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: isopropyl alcohol / 4 h / Reflux 5.1: trichlorophosphate / 2 h / Reflux 5.2: pH 10 6.1: hydrogenchloride / ethanol; water / Heating View Scheme

Yield

Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: isopropyl alcohol / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 10
6.1: hydrogenchloride / ethanol; water / Heating
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 9-fluoro-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline mesylate

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: hydrogenchloride / isopropyl alcohol; water 5.1: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / cooling with ice 6.1: ethanol / 0.5 h / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / isopropyl alcohol; water
5.1: triethylamine; methanesulfonyl chloride / toluene / 7 h / 20 °C / cooling with ice
6.1: ethanol / 0.5 h / Reflux
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 9-ethynyl-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: pyridine / acetonitrile / 4 h / Reflux 5.1: trichlorophosphate / 2 h / Reflux 5.2: pH 9 6.1: hydrogenchloride / ethanol; water / Heating 7.1: triethylamine / triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux 8.1: sodium hydroxide / toluene / 6 h / Inert atmosphere; Reflux 9.1: hydrogenchloride / ethanol View Scheme

Yield

Multi-step reaction with 9 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 9
6.1: hydrogenchloride / ethanol; water / Heating
7.1: triethylamine / triphenylphosphine; palladium diacetate; copper(l) iodide / 7 h / Inert atmosphere; Reflux
8.1: sodium hydroxide / toluene / 6 h / Inert atmosphere; Reflux
9.1: hydrogenchloride / ethanol
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 9-amino-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrobromide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C 5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice 6.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux 7.1: hydrogen bromide / ethyl acetate; ethanol View Scheme

Yield

Multi-step reaction with 7 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: hydrogenchloride / 1,4-dioxane; water / 7 h / 20 °C
5.1: triethylamine; methanesulfonyl chloride / chloroform / 20 °C / cooling with ice
6.1: hydrogen / palladium 10% on activated carbon / methanol / 5 h / 760.05 Torr / Reflux
7.1: hydrogen bromide / ethyl acetate; ethanol
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347720-70-0
C21H24ClN3O5

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: isopropyl alcohol / 4 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: isopropyl alcohol / 4 h / Reflux View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347720-73-3
C21H24BrN3O5

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: pyridine / acetonitrile / 4 h / Reflux View Scheme
Multi-step reaction with 4 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: pyridine / acetonitrile / 4 h / Reflux View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 9-bromo-2,3-bis(2-methoxyethoxy)-8H-quinazolino[4,3-b]quinazoline hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: pyridine / acetonitrile / 4 h / Reflux 5.1: trichlorophosphate / 2 h / Reflux 5.2: pH 9 6.1: hydrogenchloride / ethanol; water / Heating View Scheme

Yield

Multi-step reaction with 6 steps
1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water
2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C
3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux
3.2: 0.5 h / 20 °C / pH 7 - 8
4.1: pyridine / acetonitrile / 4 h / Reflux
5.1: trichlorophosphate / 2 h / Reflux
5.2: pH 9
6.1: hydrogenchloride / ethanol; water / Heating
View Scheme

: 183322-16-9
3,4-bis(2-methoxyethoxy)benzoic acid ethyl ester

: 1347720-76-6
C21H24FN3O5

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: nitric acid / acetic acid / 24 h / 20 °C / cooling with ice-water 2.1: ammonium formate / 5%-palladium/activated carbon / 7 h / 150 °C 3.1: thionyl chloride / N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 3.2: 0.5 h / 20 °C / pH 7 - 8 4.1: hydrogenchloride / isopropyl alcohol; water View Scheme
Multi-step reaction with 4 steps 1: nitric acid; acetic acid / 24 h / 20 °C / Cooling with ice 2: ammonium formate; 5%-palladium/activated carbon / 7 h / 150 °C 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 6 h / Reflux 4: hydrogenchloride / isopropyl alcohol; water / 20 °C View Scheme

Ethyl 3,4-bis(2-methoxyethoxy)benzoate Specification

The Ethyl 3,4-bis(2-methoxyethoxy)benzoate with cas registry number of 183322-16-9, has the systematic name of ethyl 3,4-bis(2-methoxyethoxy)benzoate. And it is also named benzoic acid, 3,4-bis(2-methoxyethoxy)-, ethyl ester.

Physical properties about this chemical are: (1)ACD/LogP: 1.93; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 6; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 11; (6)Polar Surface Area: 63.22 Å²; (7)Index of Refraction: 1.488; (8)Molar Refractivity: 78.03 cm³; (9)Molar Volume: 270.5 cm³; (10)Polarizability: 30.93×10^-24cm³; (11)Surface Tension: 36.1 dyne/cm; (12)Enthalpy of Vaporization: 65.28 kJ/mol; (13)Vapour Pressure: 1.15E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)c1cc(OCCOC)c(OCCOC)cc1;
(2)InChI: InChI=1/C15H22O6/c1-4-19-15(16)12-5-6-13(20-9-7-17-2)14(11-12)21-10-8-18-3/h5-6,11H,4,7-10H2,1-3H3;
(3)InChIKey: VGFZRAVMWXHEJB-UHFFFAOYAU;
(4)Std. InChI: InChI=1S/C15H22O6/c1-4-19-15(16)12-5-6-13(20-9-7-17-2)14(11-12)21-10-8-18-3/h5-6,11H,4,7-10H2,1-3H3;
(5)Std. InChIKey: VGFZRAVMWXHEJB-UHFFFAOYSA-N

Product Name

Ethyl 3,4-bis(2-methoxyethoxy)benzoate

Synthetic route

Ethyl 3,4-bis(2-methoxyethoxy)benzoate Specification

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