Sodium Hydroxide → (S)-3-(Benzyloxy)butanoic acid

Participants

Reaction Steps

To a solution of the above ethyl (3S)-3-(benzyloxy)butanoic acid ethyl ester (339 g) in 1,4-dioxane (1.5 L), 2N aqueous sodium hydroxide solution (0.75 L, 1.5 mol) was added, and the mixture was stirred at room temperature for 3 hours. After the reaction, the solvent was distilled off under reduced pressure, and after the aqueous phase was washed with diethyl ether, concentrated hydrochloric acid (0.14 L) was added to acidify it. After it was extracted with ethyl acetate, it was successively washed with water and saturated brine, and then it was dried with sodium sulfate and the solvent was distilled off under reduced pressure to give (3S)-3-(benzyloxy)butanoic acid (254 g) as a mixture. The present compound was used for the subsequent reaction without further purification.

Provenance & Evidence