Water → Acetic acid, 5-methoxy-m-tolyl-

Participants

Reaction Steps

A solution of 1-bromomethyl-3-methoxy-5-methyl-benzene (1.66 g, 7.7 mmol) and sodium cyanide (1.89 g, 38.5 mmol) in ethanol (15 mL) and water (5 mL) was warmed to 60° C. for 2 hrs. The reaction mixture was cooled, concentrated in vacuo, diluted with water (100 mL), and extracted with methylene chloride (3×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 1.16 g of a light yellow oil. The crude 1-cyanomethyl-3-methoxy-5-methyl-benzene (1.16 g, 7.1 mmol) and sodium hydroxide (1.44 g, 35.9 mmol) in ethanol (20 mL) and water (10 mL) was refluxed overnight. The reaction mixture was cooled, concentrated in vacuo, diluted with water, and extracted with methylene chloride (3×10 mL). The aqueous layer was acidified to pH 2 with 6N hydrochloric acid and extracted with methylene chloride (3×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 0.86 g (62% for 2 steps) of (3-methoxy-5-methyl-phenyl)-acetic acid as an off white solid. This material was used without further purification: 1H NMR (300 MHz) compatible.

Provenance & Evidence