Sodium Hydroxide → 3-(4-Benzylphenyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3-(4-benzylphenyl)propanoate (S39, 320 mg, 1.19 mmol) in THF/MeOH (1/1, 10 mL) was treated with aqueous 4 N NaOH (1 mL) and stirred for 3 h at 25° C. The reaction mixture was concentrated, diluted with aqueous 1 N HCl and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated to afford S40 (260 mg, 1.08 mmol, 91%) as a white solid: 1H NMR (CDCl3, 500 MHz) 7.27-7.06 (m, 9H), 3.91 (s, 2H), 2.86 (br s, 2H), 2.59 (br s, 2H); 13C NMR (CDCl3, 100 MHz) 179.9, 141.1, 138.8, 138.4, 128.9, 128.8, 128.4, 128.2, 126.0, 41.4, 36.9, 30.7.

Provenance & Evidence