Water → 4-(4-Methoxyphenyl)-4-oxo-3-phenylbutanoic acid

Participants

Reaction Steps

A solution of 4-(4-methoxy-phenyl)-4-oxo-3-phenyl-butyric acid ethyl ester (5.0 g, 16 mmol) in EtOH:H2O (60 mL 1:1) was stirred as 10N NaOH (16 mL) was added dropwise. The reaction was stirred at rt for 1 hr. The solvent was evaporated and the residue was diluted with water (50 mL) and extracted with CH2Cl2 (2×20 mL). The aqueous layer was then acidified with 3N HCl to pH ˜2-3, extracted with CH2Cl2 (3×30 mL). The CH2Cl2 extracts were dried over MgSO4, and the oil was crystallized from Et2O/MeOH to give 4.5 g (99%) of 4-(4-methoxy-phenyl)-4-oxo-3-phenyl-butyric acid: mp 157-9° C.; MS m/z 283 (M−H).

Provenance & Evidence