HCID 21515491, compound → 3,5-Dimethoxy-4-(2-methylpropyl)benzoic acid

HRID 1284025Notes

Reaction equation

HRID 1284025 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:16][CH3:17])[C:11]=1[CH:12]=[C:13]([CH3:15])[CH3:14])[C:6]([OH:8])=[O:7]>C(OCC)C>[CH3:17][O:16][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[CH2:12][CH:13]([CH3:14])[CH3:15])[C:6]([OH:8])=[O:7]

Participants

3

Reactant 1

HCID 21515491HCID 21515491, compound

Product 1

HCID 215155073,5-Dimethoxy-4-(2-methylpropyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3,5-Dimethoxy-4-isobutyl-benzoyl chloride. Starting from 3-hydroxy-5-methoxy-benzoic acid methyl ester and 3-chloro-2-methyl-propene, 3-(2-methyl-2-propenyloxy)-5-methoxy-benzoic acid methyl ester is obtained. B.p. 148°-50°C/0.4 mmHg. By operating as described under C), 3,5-dimethoxy-4-(2-methylpropenyl)-benzoic acid is prepared. M.p. 159°-61°C (from diethyl ether). This compound is hydrogenated as under D) to give 3,5-dimethoxy-4-isobutyl-benzoic acid. M.p. 160°-62°C (from diethyl ether/light petroleum). The corresponding chloride melts at 48°-50°C (from ligroin upon cooling).

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-aa5a640d355c4bbebde0c9db71e4e559
Source dataset
uspto-grants-1976_08
Patent number
US03978065

Reaction notes

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