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4707-47-5

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  • China Northwest Largest Factory Manufacturer Supply METHYL 2,4-DIHYDROXY-3,6-DIMETHYLBENZOATE CAS 4707-47-5

    Cas No: 4707-47-5

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4707-47-5 Usage

Chemical Properties

Methyl 3,6-Dimethylresorcylate is an odor-determining constituent of oakmoss absolute extract and forms colorless crystals (mp 145°C) with a mossy–earthy odor.

Uses

Methyl atratate is used in biological study as role of androgens in inducing distinct response of epithelial-mesenchymal transition factors in human prostate cancer cells.

Preparation

Methyl 3,6-dimethylresorcylate is prepared by aromatization of corresponding hydroxycyclohexenones, for example, by dehydrogenation with a suitable Nhaloimide.The intermediate hydroxycyclohexenone can be obtained either by reaction of dimethylmalonate with 4-hexen-3-one and 5-chloro-3-hexanone or by reaction of methyl propionylacetate with alkyl crotonate.Another route starts from the corresponding dimethyl-1,3-dihydroxybenzene, which is carboxylated, and the resulting dihydroxymethylbenzoic acid is esterified.

Flammability and Explosibility

Notclassified

Trade name

Atralone (Agan)

Check Digit Verification of cas no

The CAS Registry Mumber 4707-47-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,0 and 7 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4707-47:
(6*4)+(5*7)+(4*0)+(3*7)+(2*4)+(1*7)=95
95 % 10 = 5
So 4707-47-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O4/c1-5-4-7(11)6(2)9(12)8(5)10(13)14-3/h4,11-12H,1-3H3

4707-47-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Veramoss

1.2 Other means of identification

Product number -
Other names Methyl atratate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4707-47-5 SDS

4707-47-5Synthetic route

2,4-dihydroxy-3,6-dimethylbenzoic acid
4707-46-4

2,4-dihydroxy-3,6-dimethylbenzoic acid

methyl iodide
74-88-4

methyl iodide

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
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%
methyl 4-hydroxy-3,6-dimethyl-2-oxycyclohex-3-enecarboxylate

methyl 4-hydroxy-3,6-dimethyl-2-oxycyclohex-3-enecarboxylate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
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
67-56-1

methanol

ethyl 2,4-dihydroxy-3,6-dimethylbenzoate
31581-32-5

ethyl 2,4-dihydroxy-3,6-dimethylbenzoate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With sodium methylate for 24h; transesterification; Heating;84%
methyl haematommate
34874-90-3

methyl haematommate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
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
127-19-5

N,N-dimethyl acetamide

methyl 3,5-dioxo-4-methylhexanoate
75950-51-5

methyl 3,5-dioxo-4-methylhexanoate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide for 10h; Product distribution; Ambient temperature; other time, reagents ratio;36%
methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
19104-04-2

methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
In methanol; water18%
Cu2 O

Cu2 O

methyl 3,6-dimethyldihydro-β-resorcylate

methyl 3,6-dimethyldihydro-β-resorcylate

methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
19104-04-2

methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In methanol10%
2,4-dihydroxy-3,6-dimethylbenzoic acid
4707-46-4

2,4-dihydroxy-3,6-dimethylbenzoic acid

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With diethyl ether
In diethyl ether
methanol
67-56-1

methanol

chloroatranorin
479-16-3

chloroatranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

methyl chlorohaemmatommate

methyl chlorohaemmatommate

Conditions
ConditionsYield
at 155℃;
ethanol
64-17-5

ethanol

atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

ethyl hematommate
39503-14-5

ethyl hematommate

Conditions
ConditionsYield
With alkali at 150℃; im Rohr;
i-Amyl alcohol
123-51-3

i-Amyl alcohol

atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

3-formyl-2,4-dihydroxy-6-methyl-benzoic acid isopentyl ester

3-formyl-2,4-dihydroxy-6-methyl-benzoic acid isopentyl ester

Conditions
ConditionsYield
With alkali at 150℃; im Rohr;
atranorin
479-20-9

atranorin

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With acetic acid
With water
With ethanol
atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

methyl haematommate
34874-90-3

methyl haematommate

Conditions
ConditionsYield
With methanol at 150℃; im Rohr;
atranorin
479-20-9

atranorin

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester
62392-82-9

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester

Conditions
ConditionsYield
With ethanol; aniline
chloroatranorin
479-16-3

chloroatranorin

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With acetic acid at 150℃;
With methanol at 150℃;
2-benzyloxy-3-formyl-4-hydroxy-6-methyl-benzoic acid methyl ester
72935-20-7

2-benzyloxy-3-formyl-4-hydroxy-6-methyl-benzoic acid methyl ester

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
Hydrogenation;
methyl 4-benzyloxy-3-formyl-2-hydroxy-6-methylbenzoate
72935-21-8

methyl 4-benzyloxy-3-formyl-2-hydroxy-6-methylbenzoate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
Hydrogenation;
2-hydroxy-4-methoxy-6-methyl-isophthalic acid-1-(3-hydroxy-4-methoxycarbonyl-2,5-dimethyl-phenyl ester)-3-methyl ester
15222-49-8

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
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid
chloroatranorin
479-16-3

chloroatranorin

acetic acid
64-19-7

acetic acid

A

3-chloro-2,6-dihydroxy-4-methylbenzaldehyde
57074-21-2

3-chloro-2,6-dihydroxy-4-methylbenzaldehyde

B

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
at 150℃;
ethanol
64-17-5

ethanol

atranorin
479-20-9

atranorin

aniline
62-53-3

aniline

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester
62392-82-9

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid ethyl ester

atranorin
479-20-9

atranorin

aniline
62-53-3

aniline

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

2,4-dihydroxy-6-methyl-3-(phenylimino-methyl)-benzoic acid methyl ester

Conditions
ConditionsYield
With methanol
N-(acetyl)pyrrolidine
4030-18-6

N-(acetyl)pyrrolidine

methyl 3,5-dioxo-4-methylhexanoate
75950-51-5

methyl 3,5-dioxo-4-methylhexanoate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide 1.) 4 h, room temperature, 2.) pH 9.2 buffer, overnight; Yield given. Multistep reaction;
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

methyl 3,5-dioxo-4-methylhexanoate
75950-51-5

methyl 3,5-dioxo-4-methylhexanoate

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

n-butyl 2,4-dihydroxy-3,6-dimethylbenzoate
75950-52-6

n-butyl 2,4-dihydroxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
With lithium diisopropyl amide for 12h; Ambient temperature;
atranorin
479-20-9

atranorin

A

orcinol
504-15-4

orcinol

B

atranol
526-37-4

atranol

C

2,5-dimethyl-1,3-benzenediol
488-87-9

2,5-dimethyl-1,3-benzenediol

D

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

E

methyl haematommate
34874-90-3

methyl haematommate

F

3-hydroxy-2,5-dimethylphenyl 2,4-dihydroxy-3,6-dimethylbenzoate

3-hydroxy-2,5-dimethylphenyl 2,4-dihydroxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
at 230 - 250℃; for 0.75h; Product distribution; pyrolysis;
1,1,4-trimethyl, 4-acetyl-ethylenediamine
20929-21-9

1,1,4-trimethyl, 4-acetyl-ethylenediamine

methyl 3,5-dioxo-4-methylhexanoate
75950-51-5

methyl 3,5-dioxo-4-methylhexanoate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide 1.) 4 h, room temperature, 2.) pH 9.2 buffer, overnight; Yield given. Multistep reaction;
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3-Methyl-2,4-pentanedione
815-57-6

3-Methyl-2,4-pentanedione

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
Multistep reaction;
chloroatranorin
479-16-3

chloroatranorin

tert-butyl alcohol
75-65-0

tert-butyl alcohol

A

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

B

tert-butyl 5-chlorohaematommate

tert-butyl 5-chlorohaematommate

Conditions
ConditionsYield
for 40h; Heating;
2.5-dimethyl-cyclohexanedione-(4.6)-carboxylic acid-(1)-methyl ester

2.5-dimethyl-cyclohexanedione-(4.6)-carboxylic acid-(1)-methyl ester

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With palladium asbestos at 150℃;
barbatic acid methyl ester

barbatic acid methyl ester

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

3-Acetoxymethyl-4,6-dimethoxy-2,5-dimethyl-benzoic acid methyl ester
148014-54-4

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
148014-55-5

(3-carbomethoxy-4,6-dihydroxy-2,5-dimethylphenyl)-(3-carbomethoxy-4,6-dimethoxy-2,5-dimethylphenyl)methane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In toluene for 0.25h; Ambient temperature;100%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

methyl iodide
74-88-4

methyl iodide

methyl 2,4-dimethoxy-3,6-dimethylbenzoate
58061-99-7

methyl 2,4-dimethoxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
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
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

methyl 3-chloro-4,6-dihydroxy-2,5-dimethylbenzoate
947-52-4

methyl 3-chloro-4,6-dihydroxy-2,5-dimethylbenzoate

Conditions
ConditionsYield
With N-chloro-succinimide In acetonitrile at 50℃; for 5h;98%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

methyl 5-bromo-2,4-dihydroxy-3,6-dimethylbenzoate
72922-67-9

methyl 5-bromo-2,4-dihydroxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
With bromine In tetrachloromethane; acetic acid for 1h; Ambient temperature;96%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

physodalic acid
90689-60-4

physodalic acid

4-formyl-3,8-dihydroxy-9-(2,4-dihydroxy-5-methoxycarbonyl-3,6-dimethylbenzyl)-1,6-dimethyl-11-oxo-11H-dibenzo<1,4>dioxepin-7-carboxylic acid

4-formyl-3,8-dihydroxy-9-(2,4-dihydroxy-5-methoxycarbonyl-3,6-dimethylbenzyl)-1,6-dimethyl-11-oxo-11H-dibenzo<1,4>dioxepin-7-carboxylic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane for 7h; Heating;96%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
19104-04-2

methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
In diethyl ether; acetone for 18h; Ambient temperature;95%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

4-O-(t-butoxycarbonyl)-2-hydroxy-3,6-dimethyl methylbenzoate
908292-00-2

4-O-(t-butoxycarbonyl)-2-hydroxy-3,6-dimethyl methylbenzoate

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane for 4h;93%
hexamethylenetetramine
100-97-0

hexamethylenetetramine

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

formyl-3-dihydroxy-4,6-dimethyl-2,5-benzoate de methyle
34874-76-5

formyl-3-dihydroxy-4,6-dimethyl-2,5-benzoate de methyle

Conditions
ConditionsYield
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;
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

methyl 2,4-bis(methoxymethoxy)-3,6-dimethylbenzoate

methyl 2,4-bis(methoxymethoxy)-3,6-dimethylbenzoate

Conditions
ConditionsYield
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%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

propargyl bromide
106-96-7

propargyl bromide

methyl 2-hydroxy-3,6-dimethyl-4-(prop-2-yn-1-yloxy) benzoate

methyl 2-hydroxy-3,6-dimethyl-4-(prop-2-yn-1-yloxy) benzoate

Conditions
ConditionsYield
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
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

C22H40O4Si2

C22H40O4Si2

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; Inert atmosphere;90%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

2-hydroxy-4-benzyloxy-3,6-dimethylbenzoic acid
56410-32-3

2-hydroxy-4-benzyloxy-3,6-dimethylbenzoic acid

methyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate
111258-35-6

methyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
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
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

2-methoxy-4-(4-methoxybenzyloxy)-3,6-dimethylbenzoic acid
261174-54-3

2-methoxy-4-(4-methoxybenzyloxy)-3,6-dimethylbenzoic acid

C28H30O8

C28H30O8

Conditions
ConditionsYield
With trifluoroacetic anhydride In toluene at 20℃; Esterification;82%
Allyl acetate
591-87-7

Allyl acetate

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

C13H16O4

C13H16O4

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 110℃; for 3h;80%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

2-hydroxy-4-methoxy-3,6-dimethylbenzoic acid
479-26-5

2-hydroxy-4-methoxy-3,6-dimethylbenzoic acid

methyl barbatate
5014-22-2

methyl barbatate

Conditions
ConditionsYield
With trifluoroacetic anhydride In toluene at 20℃; Esterification;77%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

2-methoxy-4-benzyloxy-3,6-dimethylbenzoic acid
125304-84-9

2-methoxy-4-benzyloxy-3,6-dimethylbenzoic acid

C27H28O7
261174-77-0

C27H28O7

Conditions
ConditionsYield
With trifluoroacetic anhydride In toluene at 20℃; Esterification;74%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

2,4-dihydroxy-3,6-dimethylbenzoic acid
4707-46-4

2,4-dihydroxy-3,6-dimethylbenzoic acid

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -70 - 20℃; for 12h;74%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

ethylene dibromide
106-93-4

ethylene dibromide

methyl 4-(2-bromoethoxy)-2-hydroxy-3,6-dimethylbenzoate

methyl 4-(2-bromoethoxy)-2-hydroxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;73%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

2,4-O-dimethyl-β-orcinolcarboxylic acid
56410-34-5

2,4-O-dimethyl-β-orcinolcarboxylic acid

4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester
81050-84-2

4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester

Conditions
ConditionsYield
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
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

2-hydroxy-4-(4-methoxybenzyloxy)-3,6-dimethylbenzoic acid
261174-53-2

2-hydroxy-4-(4-methoxybenzyloxy)-3,6-dimethylbenzoic acid

C27H28O8

C27H28O8

Conditions
ConditionsYield
With trifluoroacetic anhydride In toluene at 20℃; Esterification;69%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

acetic anhydride
108-24-7

acetic anhydride

4-(methoxycarbonyl)-2,5-dimethyl-1,3-phenylene diacetate
57369-96-7

4-(methoxycarbonyl)-2,5-dimethyl-1,3-phenylene diacetate

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;68%
With pyridine
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

allyl bromide
106-95-6

allyl bromide

methyl 4-(allyloxy)-2-hydroxy-3,6-dimethylbenzoate

methyl 4-(allyloxy)-2-hydroxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;53%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

methyl iodide
74-88-4

methyl iodide

methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate
19104-04-2

methyl 2-hydroxy-4-methoxy-3,6-dimethylbenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;50%
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
4707-47-5

2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester

allyl bromide
106-95-6

allyl bromide

methyl 2,4-bis(allyloxy)-3,6-dimethylbenzoate

methyl 2,4-bis(allyloxy)-3,6-dimethylbenzoate

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;47%

4707-47-5Relevant articles and documents

-

Fujii,Osumi

, (1936)

-

Two new glycosides from Dianella ensifolia (L.) DC

Fan, Miao-Yin,Liu, Bing-Rui,Yang, Fan,Zhang, Pu-Zhao

, p. 18 - 20 (2021/11/11)

The Dianella genus includes approximately 20 species in all over the world. So far, only the chemical constituents of the lipophilic extract from Dianella ensifolia have been investigated. However, there have been no reports of its aqueous extract. In thi

Compositional variation of atranorin-related components of lichen Myelochroa leucotyliza dependent on extraction solvent and their quantitative analysis by qHNMR

Ojha, Manju,Kil, Yun-Seo,Youn, Ui Joung,Ok, Young Jun,Choi, Hyukjae,Nam, Joo-Won

, p. 1067 - 1073 (2021/04/05)

Introduction: Quantitative nuclear magnetic resonance (qNMR) is one of the effective and reliable quantification tools for natural product research. Myelochroa leucotyliza belongs to the genus Myelochroa, a common foliose lichen genus found in the Korean Peninsula, and has not been quantitatively analysed using NMR. Previous chemical studies on M. leucotyliza have been limited to the main components by traditional thin-layer chromatography (TLC) experiments. Objective: We explored the stability of atranorin, a major component of M. leucotyliza, in methanol and acetone using NMR and characterised the changes in the chemical profiles of the lichen extracts in methanol and acetone using qNMR. Methodology: Atranorin transformation in the presence of methanol was analysed using time-dependent proton (1H)-NMR analysis (600 MHz NMR spectrometer). A 1H qNMR (qHNMR) method was established using dimethyl sulfone as the internal standard for quantifying the selected components isolated from M. leucotyliza. Homogenous mixtures of the samples were dissolved in deuterated chloroform. Results: Time-dependent 1H-NMR experiments revealed that atranorin (5) from lichen M. leucotyliza decomposed into atraric acid (1) and methyl haemmatommate (2) in methanol. Four components were identified from M. leucotyliza: 1, 2, usnic acid (4), and 5, and their respective contents were determined using qHNMR. The percentages (w/w) of 1, 2, and 4 in the methanol extract were calculated as 5.66%, 0.69%, and 0.90%, while those of 1, 4, and 5 in the acetone extract were 1.70%, 1.68%, and 19.11%, respectively. Conclusion: We used qHNMR to effectively analyse quantitative compositional variations in two different M. leucotyliza extracts and reliably determined the chemical conversion of the unstable compound atranorin.

Method for aromatizing synthetic oak moss

-

Paragraph 0021; 0023-0028, (2019/01/14)

The invention provides a method for aromatizing synthetic an oak moss. The method comprises the following steps: adding chlorinated 2,5dimethyl-dihydro-methyl resorcylate into a solvent acetonitrile for aromatization reaction; then carrying out cooling crystallization to obtain a coarse product of the synthetic oak moss. Compared with the prior art, the method for aromatizing the oak moss, disclosed by the invention, has the following advantages: firstly, the by-product sodium chloride produced by the reaction can be directly filtered; secondly, reactive water can be recycled; thirdly, when the aromatization reaction is carried out, the reaction is not drastic because the reaction occurs in the acetonitrile solvent, and the generated hydrogen chloride is easy to recover; fourthly, an aftertreatment process is simple and the purity of the produced crude product reaches 98 percent or above. Therefore, the method provides an improved process method for the synthetic oak moss, which is environmentally friendly and energy saving and can be used for industrial production.

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