Hydrochloric Acid → 5-(Benzyloxy)pentanoic acid

Participants

Reaction Steps

A mixture of 100 g of δ-valerolactone, 50 ml of water, 350 ml of toluene, 280g of potassium hydroxide pellets and 300 ml of benzyl chloride is refluxed overnight with mechanical stirring and azeotroping the water with the use of a Dean-Stark apparatus. The thick white mass is cooled to room temperature and dissolved in 1 l of cold water. The organic layer is separated and the aqueous layer is condensed to 1/3 by heating over a period of 5 h. The mixture is cooled to room temperature, acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×300 ml). The combined extracts are washed with brine, dried (MgSO4) and evaporated to dryness to give 5-benzyloxypentanoic acid.

Provenance & Evidence