Acetic Acid → Benzyl 3-benzyloxy-5-aminobenzoate

Participants

Reaction Conditions

Reaction Steps

2.52 g (38.5 mmol) Zn were suspended in 6 mL methylene chloride (dry, distilled), 0.9 mL (15.7 mmol) acetic acid were added and the suspension was cooled to 0° C. A solution of 0.7 g (1.93 mmol) nitrobenzoate 12 in 2 mL methylene chloride was added by syringe. After 2 h of stirring, TLC (hexanes/ethyl acetate, 7:3, Rf=0.4) indicated complete conversion of starting material. Zn was filtered off and the filtrate was concentrated, taken up in ethyl acetate and washed with aqueous NaHCO3 three times, then with brine. After drying with MgSO4 and evaporation, an orange-brown oil was obtained, which was purified by column chromatography (hexanes/ethyl acetate, 7:3) to afford 310 mg (48%) of a yellow oil. 1H NMR (CDCl3) δ 7.50-7.27 (m, 10H), 7.12 (dd, J1=1.3 Hz, J2=2.2 Hz, 1H), 7.02 (dd, J1=1.3 Hz, J2=2.2 Hz, 1H), 6.49 (t, J1=2.2 Hz, J2=2.2 Hz, 1H), 5.38 (s, 2H, PhCH2), 5.03 (s, 2H), 3.69 (s, 2H, PhCH2).

Provenance & Evidence