2,4-dihydroxy-3,6-dimethylbenzoic acid
methyl iodide
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 2,4-dihydroxy-3,6-dimethylbenzoic acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃; for 0.166667h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide for 1.41667h; Inert atmosphere; | 90.4% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With copper(II) choride dihydrate; sodium chloride In acetonitrile at 85℃; for 5h; | 88.7% |
With copper(II) choride dihydrate; sodium chloride In acetonitrile at 85℃; for 5h; | 88.7% |
With copper(II) choride dihydrate; sodium chloride In acetonitrile at 85℃; for 5h; | 88.7% |
With copper(II) choride dihydrate; sodium chloride In acetonitrile at 85℃; for 5h; | 88.7% |
With copper(II) choride dihydrate; sodium chloride In acetonitrile at 85℃; for 5h; | 88.7% |
methanol
ethyl 2,4-dihydroxy-3,6-dimethylbenzoate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With sodium methylate for 24h; transesterification; Heating; | 84% |
methyl haematommate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; mercury; zinc In methanol Reduction; | 78% |
With hydrogenchloride; amalgamated zinc | |
Multi-step reaction with 2 steps 1: sodium iodide; potassium carbonate; acetone 2: Hydrogenation View Scheme | |
Multi-step reaction with 2 steps 1: sodium iodide; potassium carbonate; acetone 2: Hydrogenation View Scheme |
N,N-dimethyl acetamide
methyl 3,5-dioxo-4-methylhexanoate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With lithium diisopropyl amide for 10h; Product distribution; Ambient temperature; other time, reagents ratio; | 36% |
methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
In methanol; water | 18% |
methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In methanol | 10% |
diazomethane
2,4-dihydroxy-3,6-dimethylbenzoic acid
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With diethyl ether | |
In diethyl ether |
methanol
chloroatranorin
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
at 155℃; |
ethanol
atranorin
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
B
ethyl hematommate
Conditions | Yield |
---|---|
With alkali at 150℃; im Rohr; |
i-Amyl alcohol
atranorin
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With alkali at 150℃; im Rohr; |
Conditions | Yield |
---|---|
With acetic acid | |
With water | |
With ethanol |
atranorin
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
B
methyl haematommate
Conditions | Yield |
---|---|
With methanol at 150℃; im Rohr; |
atranorin
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
B
2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester
Conditions | Yield |
---|---|
With ethanol; aniline |
Conditions | Yield |
---|---|
With acetic acid at 150℃; | |
With methanol at 150℃; |
2-benzyloxy-3-formyl-4-hydroxy-6-methyl-benzoic acid methyl ester
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
Hydrogenation; |
methyl 4-benzyloxy-3-formyl-2-hydroxy-6-methylbenzoate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
Hydrogenation; |
2-hydroxy-4-methoxy-6-methyl-isophthalic acid-1-(3-hydroxy-4-methoxycarbonyl-2,5-dimethyl-phenyl ester)-3-methyl ester
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid |
chloroatranorin
acetic acid
A
3-chloro-2,6-dihydroxy-4-methylbenzaldehyde
B
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
at 150℃; |
ethanol
atranorin
aniline
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
B
2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester
Conditions | Yield |
---|---|
With methanol |
N-(acetyl)pyrrolidine
methyl 3,5-dioxo-4-methylhexanoate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) 4 h, room temperature, 2.) pH 9.2 buffer, overnight; Yield given. Multistep reaction; |
N,N-dimethyl acetamide
methyl 3,5-dioxo-4-methylhexanoate
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
B
n-butyl 2,4-dihydroxy-3,6-dimethylbenzoate
Conditions | Yield |
---|---|
With lithium diisopropyl amide for 12h; Ambient temperature; |
atranorin
A
orcinol
B
atranol
C
2,5-dimethyl-1,3-benzenediol
D
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
E
methyl haematommate
Conditions | Yield |
---|---|
at 230 - 250℃; for 0.75h; Product distribution; pyrolysis; |
1,1,4-trimethyl, 4-acetyl-ethylenediamine
methyl 3,5-dioxo-4-methylhexanoate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) 4 h, room temperature, 2.) pH 9.2 buffer, overnight; Yield given. Multistep reaction; |
N,N-dimethyl acetamide
carbonic acid dimethyl ester
3-Methyl-2,4-pentanedione
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
Multistep reaction; |
chloroatranorin
tert-butyl alcohol
A
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
for 40h; Heating; |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With palladium asbestos at 150℃; |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
3-Acetoxymethyl-4,6-dimethoxy-2,5-dimethyl-benzoic acid methyl ester
(3-carbomethoxy-4,6-dihydroxy-2,5-dimethylphenyl)-(3-carbomethoxy-4,6-dimethoxy-2,5-dimethylphenyl)methane
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In toluene for 0.25h; Ambient temperature; | 100% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
methyl iodide
methyl 2,4-dimethoxy-3,6-dimethylbenzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; Inert atmosphere; | 98% |
With potassium carbonate In acetone Reflux; | 50% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
methyl 3-chloro-4,6-dihydroxy-2,5-dimethylbenzoate
Conditions | Yield |
---|---|
With N-chloro-succinimide In acetonitrile at 50℃; for 5h; | 98% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
methyl 5-bromo-2,4-dihydroxy-3,6-dimethylbenzoate
Conditions | Yield |
---|---|
With bromine In tetrachloromethane; acetic acid for 1h; Ambient temperature; | 96% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
physodalic acid
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,4-dioxane for 7h; Heating; | 96% |
diazomethane
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
Conditions | Yield |
---|---|
In diethyl ether; acetone for 18h; Ambient temperature; | 95% |
di-tert-butyl dicarbonate
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4-O-(t-butoxycarbonyl)-2-hydroxy-3,6-dimethyl methylbenzoate
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; | 93% |
hexamethylenetetramine
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
formyl-3-dihydroxy-4,6-dimethyl-2,5-benzoate de methyle
Conditions | Yield |
---|---|
With trifluoroacetic acid Formylation; Duff formylation; | 90% |
Stage #1: hexamethylenetetramine; 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester With trifluoroacetic acid at 0℃; for 2.5h; Inert atmosphere; Reflux; Stage #2: With water for 2.5h; Inert atmosphere; Reflux; | 76% |
With water; trifluoroacetic acid 1.) reflux, 14 h; 2.) 65 deg C, 8 h; Yield given. Multistep reaction; | |
With water; trifluoroacetic acid 1.) reflux, 12 h; 2.) 60 deg C, 6 h; Yield given. Multistep reaction; | |
With trifluoroacetic acid for 20h; Inert atmosphere; Reflux; |
Conditions | Yield |
---|---|
Stage #1: 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; Inert atmosphere; Schlenk technique; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere; Schlenk technique; | 90% |
Stage #1: 2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: chloromethyl methyl ether In tetrahydrofuran; toluene at 25℃; for 3h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 12h; | 90% |
With potassium carbonate In acetone Reflux; | 75% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
t-butyldimethylsiyl triflate
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 90% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
2-hydroxy-4-benzyloxy-3,6-dimethylbenzoic acid
methyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
Conditions | Yield |
---|---|
With trifluoroacetic anhydride In toluene Ambient temperature; | 84% |
With trifluoroacetic anhydride In toluene at 20℃; Esterification; | 63% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
2-methoxy-4-(4-methoxybenzyloxy)-3,6-dimethylbenzoic acid
Conditions | Yield |
---|---|
With trifluoroacetic anhydride In toluene at 20℃; Esterification; | 82% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 110℃; for 3h; | 80% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
2-hydroxy-4-methoxy-3,6-dimethylbenzoic acid
methyl barbatate
Conditions | Yield |
---|---|
With trifluoroacetic anhydride In toluene at 20℃; Esterification; | 77% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
2-methoxy-4-benzyloxy-3,6-dimethylbenzoic acid
C27H28O7
Conditions | Yield |
---|---|
With trifluoroacetic anhydride In toluene at 20℃; Esterification; | 74% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
2,4-dihydroxy-3,6-dimethylbenzoic acid
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -70 - 20℃; for 12h; | 74% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 73% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
2,4-O-dimethyl-β-orcinolcarboxylic acid
4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester
Conditions | Yield |
---|---|
With trifluoroacetic anhydride In toluene at 20℃; Esterification; | 69% |
With sodium hydroxide; thionyl chloride; acetone |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
2-hydroxy-4-(4-methoxybenzyloxy)-3,6-dimethylbenzoic acid
Conditions | Yield |
---|---|
With trifluoroacetic anhydride In toluene at 20℃; Esterification; | 69% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
acetic anhydride
4-(methoxycarbonyl)-2,5-dimethyl-1,3-phenylene diacetate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 12h; | 68% |
With pyridine |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 53% |
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
methyl iodide
methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 50% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 47% |
The Methyl 2,4-dihydroxy-3,6-dimethylbenzoate, with the CAS registry number 4707-47-5 and EINECS registry number 225-193-0, is also called 2,4-Dihydroxy-3,6-dimethyl-benzoic acid methyl ester. The molecular formula of the chemical is C10H12O4. And the chemical belongs to the following product categories: Alphabetical Listings; Flavors and Fragrances; M-N.
The characteristics of this chemical are as followings: (1)ACD/LogP: 2.84; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.84; (4)ACD/LogD (pH 7.4): 2.81; (5)ACD/BCF (pH 5.5): 84.52; (6)ACD/BCF (pH 7.4): 79.68; (7)ACD/KOC (pH 5.5): 833.35; (8)ACD/KOC (pH 7.4): 785.6; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.57; (14)Molar Refractivity: 51.43 cm3; (15)Molar Volume: 156.7 cm3; (16)Polarizability: 20.39×10-24cm3; (17)Surface Tension: 50.3 dyne/cm; (18)Density: 1.251 g/cm3; (19)Flash Point: 143.9 °C; (20)Enthalpy of Vaporization: 63.03 kJ/mol; (21)Boiling Point: 360.7 °C at 760 mmHg; (22)Vapour Pressure: 1.05E-05 mmHg at 25°C.
Preparation of Methyl 2,4-dihydroxy-3,6-dimethylbenzoate: This chemical can be prepared by 3-formyl-2,4-dihydroxy-6-methyl-benzoic acid methyl ester. The reaction will need reagent Zn(Hg) and HCl, and the menstruum methanol. The yield is about 16%.
Uses of Methyl 2,4-dihydroxy-3,6-dimethylbenzoate: It can react with 2,4-dimethoxy-3,6-dimethyl-benzoic acid to produce 4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester. This reaction will need reagent (CF3-CO)2O, and the menstruum toluene. The temperature of the reaction is 20°C, and the yield is about 69%.
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(OC)c1c(cc(O)c(c1O)C)C
(2)InChI: InChI=1/C10H12O4/c1-5-4-7(11)6(2)9(12)8(5)10(13)14-3/h4,11-12H,1-3H3
(3)InChIKey: UUQHKWMIDYRWHH-UHFFFAOYAK
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