Hydrochloric Acid → 2-(4-(Benzyloxy)phenyl)-2-hydroxyacetic acid

Participants

Reaction Steps

A solution of 41.6 g (0.20 mol) of sodium 4-hydroxymandelate monohydrate, 9.6 g (0.24 mol) of sodium hydroxide and 27.9 g (0.22 mol) of benzyl chloride in 50 ml of water is stirred at 70° C. for 17 hours. The mixture is then diluted with 50 ml of water, and another 4.0 g (0.10 mol) of sodium hydroxide are added. The reaction mixture is refluxed for one hour, then cooled, acidified with concentrated hydrochloric acid, and the precipitated product is filtered. The residue is washed with cold water and then dried in a high vacuum, giving 35.6 g (69%) of 4-benzyloxymandelic acid, melting point 148°-155° C.

Provenance & Evidence