Water → Methyl 3-{4-[(3-aminobenzyl)oxy]phenyl}-propanoate

Participants

Reaction Steps

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (5.10 g, 28.3 mmol) in N,N-dimethylformamide (40 mL) was added sodium hydride (in oil, 1.20 g, 30 mmol) at 0° C. and the mixture was stirred at the same temperature for 1 hr. 3-Nitrobenzylbromide (6.72 g, 31.1 mmol) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a yellow oil. To a mixture of the obtained oil, tetrahydrofuran (50 mL) and ethanol (50 mL) was added platinum dioxide (350 mg) and the mixture was stirred under a hydrogen atmosphere for 16 hr. Insoluble materials were filtered off, and the filtrate was concentrated to give the title compound (7.73 g, yield 96%, 2 steps) as pale-yellow crystals.

Provenance & Evidence