4-Fluorophenol → 3-(4-Fluorophenoxy)propionic acid

Participants

Reaction Steps

To 83 g. of sodium hydride in 100 ml. of dry dimethoxyethane at 5° C. was added a solution of 15.3 g. of 2-bromopropionic acid in 50 ml. of dimethoxyethane and 10.5 g. of 4-fluorophenol in 50 ml. of dimethoxyethane. The slurry was heated to reflux for 6 hours, cooled and filtered. The crude solid was partitioned between methylenechloride and 1 N hydrochloric acid and this process repeated. The organic layer was dried and evaporated to 50 ml. The crystals were collected, washed with hexane and dried, m.p. 113°-115° C.

Provenance & Evidence