Potassium Hydroxide → alpha-Methyl-3-fluorocinnamic acid

Participants

Reaction Steps

A mixture of 49.6 g. (0.4 mole) of meta-fluorobenzaldehyde, 66 ml. (0.51 mole) of propionic anhydride and 38.4 g. (0.4 mole) of sodium propionate were heated at 135°C for 19 hours. The reaction was cooled and to it was added a liter of 1 normal potassium hydroxide and the mixture was extracted with ether. The aqueous phase was freed of residual ether and acidified to pH 2 with hydrochloric acid. The product which crystallized was filtered and dried to give 51.5 grams of α-methyl-3-fluorocinnamic acid, melting point 95°-97°C.

Provenance & Evidence