Acetyl chloride → Benzoic acid, 3-methoxy-4-methyl-, methyl ester

HRID 615493Notes

Reaction equation

HRID 615493 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=[O:7].[C:13](Cl)(=O)C>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([O:8][CH3:13])=[O:7]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 815794-Methyl-m-anisic acid

Product 1

HCID 591123Benzoic acid, 3-methoxy-4-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6.0 g (36.1 mmoles) of 3-methoxy-4-methylbenzoic acid in 120 ml of anhydrous MeOH was treated with 6 ml of acetyl chloride and stirred at room temperature for 36 hours. The MeOH was evaporated in vacuo followed by addition and evaporation of two 100 ml portion of methanol to give 6.34 g of methyl 3-methoxy-4-methylbenzoate colorless oil. This was carried through steps analogous to those in Example 1, steps b., c. and d.

Workup

  1. customThe MeOH was evaporated in vacuo
  2. additionfollowed by addition and evaporation of two 100 ml portion of methanol

Sources & evidence

ORD record
ord-376ffd188f504ea49ccc302bd13a8093
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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