Acetyl chloride → HCID 53767267, compound

Participants

Reaction Steps

A solution of 4.3 g (13.96 mmol) of 2-[[5-(acetoxy)pentyl]oxy]benzenepropanoic acid methyl ester and 2.18 g (27.8 mmol) of freshly distilled acetyl chloride in 250 mL of dry dichloromethane was stirred with ice-bath cooling while 7.5 g (56.7 mmol) of anhydrous aluminum chloride was added in one portion. The resulting mixture was stirred at 0°-5° C. for 2 hr before being treated with ice. Work-up with dichloromethane in the usual manner gave an oil which was chromatographed on 100 g of silica gel. Elution with 1:1 hexane-ether afforded 4.22 g (86.4%) of 2-[[5-(acetoxy)pentyl]oxy]-5-acetylbenzenepropanoic acid methyl ester as an almost colorless oil.

Provenance & Evidence