Hydrochloric Acid → 3-(4-Benzyloxyphenyl)propionic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-hydroxyphenyl)propionic acid (20.0 g, 0.12 mol) and benzyl bromide (21.5 mL, 0.18 mol) in 155 mL of THF is added, at ambient temperature to a 1N aqueous solution of soda (301 mL). The phase transfer catalyst, Bu4NHSO4 (155 mg, 0.45 mmol), is finally added. The reaction medium is stirred overnight before being heated for 1 h at 80° C. After cooling down, 150 mL of a 1N aqueous solution of HCl is added slowly. After extraction with CH2Cl2, the organic phases are dried over MgSO4, filtered and concentrated under vacuum. Purification is carried out on silica gel (CH2Cl2 up to CH2Cl2/MeOH 95:5) in order to produce compound 2 (30.4 g, 0.12 mol, 99%) in the form of a white solid.

Provenance & Evidence