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

Participants

Reaction Steps

To a stirred slurry of 8.3 g of sodium hydride (57° 10 NaH in oil) in 100 ml of dry 1,2-dimethoxyethane at 5° C. is added 15.3 g of 2-bromopropionic acid in 50 ml of 1,2-dimethoxyethane and 10.5 g of 4-fluorophenol in 50 ml of 1,2-dimethoxyethane. The mixture is refluxed for 6 hrs, cooled and filtered. The solid is partitioned between dichloromethane and 1N HCl. The organic layer is dried (MgSO4) and concentrated to 50 ml. The mixture is filtered to give 10.4 g of product, mp 113°-115° C.

Provenance & Evidence