Benzyl Alcohol → (Benzyloxy)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of KOH (17.84 g, 118 mmol) in THF (200 mL) was added benzyl alcohol (42 mL, 424 mmol). After 1.5 h the mixture was heated to 50° C. for 1.5 h and cooled to rt afterwards. Chloroacetic acid (10 g, 106 mmol) was added and the mixture was heated to 80° C. After 1.5 h the mixture was cooled to rt and water and MTBE was added. The layers were separated, the aqueous layer was extracted with MTBE, the pH of the aqueous layer was adjusted to pH=2 with 6N HCl and extracted with MTBE. The extracts of the acidic layer were dried and the solvent removed under reduced pressure to give 12.4 g of the crude product.

Provenance & Evidence