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

HRID 1904457Notes

Reaction equation

HRID 1904457 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 as a colorless oil (6.34 g, 98%); NMR: 2.2(s, 3H, CH3), 3.9(2s, 6H, 2xOCH3), 7.1(d, 1H), 7.5(m, 2H). A solution of ester prepared according to the method described above (121.2 g) in carbon tetrachloride (1400 ml) was heated under gentle reflux with a 350 watt tungsten lamp and subjected to an air purge by means of a T-tube attached to a water aspirator. A solution of bromine (107.2 g) in carbon tetrachloride (500 ml) was added dropwise over 4 hours. Evaporation of the solvent gave a light yellow solid which was triturated with a solution (500 ml) of 1:9 (v/v) ether:hexane. The solid was collected by filtration to give methyl 4-bromomethyl-3-methoxybenzoate (111.7 g, 64%) as a light yellow solid; mp 87°-90° C.; NMR: 3.9(2s, 6H, 2xOCH3), 4.5(s, 2H, BrCH2), 7.4(m, 3H).

Workup

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

Sources & evidence

ORD record
ord-aa576ca22ff9453490eea1fcc9023595
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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