Water → Methyl 3-chloro-p-anisate

Participants

Reaction Steps

To a cooled solution of 14.5 g. (0.078 mol.) of 3-chloro-4-hydroxybenzoic acid methyl ester and 4.0 g. (0.1 mol.) of sodium hydroxide in 100 ml. of water was dropwise added 9.8 g. (7.3 ml., 0.079 mol.) of dimethyl sulfate. The reaction mixture was refluxed for two hours. After cooling, ether was added and the layers were separated. The organic phase was washed with water, dilute sulfuric acid and water, dried (Na2SO4) and concentrated in vacuo to give 3-chloro-4-methoxybenzoic acid methyl ester, m.p. 72°-74°.

Provenance & Evidence