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

HRID 2073546Notes

Reaction equation

HRID 2073546 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 esterYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-methoxy-4-methylbenzoic acid (6.0 g) in methanol (120 ml) was treated with acetyl chloride (6 ml) and stirred for 36 hours. The solution was evaporated. The residue was dissolved in methanol (100 ml) and the solution evaporated. This procedure was repeated to give methyl 3-methoxy-4-methylbenzoate (6.34 g, 98%) as a colorless oil; NMR (80 MHz, CDCl3): 2.2(s, 3H, CH3), 3.9(2s, 6H, 2×OCH3), 7.1(d, 1H), 7.5(m, 2H).

Workup

  1. customThe solution was evaporated
  2. dissolutionThe residue was dissolved in methanol (100 ml)
  3. customthe solution evaporated

Sources & evidence

ORD record
ord-4ffce73ccd98470792325bdc39d27792
Source dataset
uspto-grants-1990_04
Patent number
US04918094

Reaction notes

Loading…