Bromoacetate → 2-(2-(Benzyloxy)ethoxy)acetic acid

Participants

Reaction Steps

This solution of bromoacetate is added dropwise to the prepared solution of benzyloxyethanolate anion, and the mixture is heated at reflux for 19 h. The reaction is stopped with 5% KHSO4. 250 ml ethyl acetate is added and the organic phase is extracted three times with the aid of 5% NaOH. The pH of the alkaline phase is reduced to 1 with 10% HCl and extraction is performed twice with EtOAc. The organic phase is washed three times with sodium chloride solution, dried on Na2SO4, and evaporated to obtain 6.4 g (93%) 7-phenyl-3,6-dioxaheptanoic acid in the form of a colourless liquid.

Provenance & Evidence