Sodium Hydroxide → 3-(4-Benzyloxyphenyl)propionic acid

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Reaction Steps

An aqueous solution of NaOH (1 M, 270 mL) was added to a mixture of the 3-(4-benzyloxyphenyl)propionic acid methyl ester from Step 2 above in MeOH (600 mL) and the reaction was stirred overnight. The crystalline ppt was collected by filtration, air dried and then partitioned between EtOAc/Et2O/1 M HCl (500 mL, 250 mL, 150 mL). The organic phases were dried over MgSO4 and evaporated to give the product as a white solid (16.2 g, 70%, 3 Steps). 1H NMR (CDCl3) δ 2.61-2.68 (m, 2H), 2.86-2.93 (m, 2H), 5.03 (s, 2H), 6.88-6.93 (m, 2H), 7.10-7.15 (m, 2H), 7.28-7.45 (m, 5H).

Provenance & Evidence