4-Acetylphenylboronic acid → Ethyl (4-acetylphenyl)acetate

Participants

Reaction Steps

Ethyl 4-acetylphenylacetate was prepared by the general experimental method from 4-acetylphenylboronic acid (164 mg, 1.00 mmol). After workup by column chromatography (hexane/ethyl acetate, 5:1), ethyl 4-acetylphenylacetate is obtained as a colourless solid in a yield of 60% of theory. 1H NMR (400 MHz, CDCl3): δ=7.90 (d, J=8.2 Hz, 2H), 7.37 (d, J=8.5 Hz, 2H), 4.11-4.17 (m, 2H), 3.66 (s, 2H), 2.58 (s, 3H), 1.20-1.27 (m, 3H) ppm; 13C NMR (151 MHz, CDCl3): δ=197.7, 170.8, 139.5, 136.0, 129.6, 128.6, 61.1, 41.3, 26.6, 14.2 ppm; MS (70 eV), m/z (%): 192 (100), 164 (16), 134 (14), 105 (19), 89 (11); IR (KBr): ν=2981 (w), 1735 (s), 1682 (m), 1274 (m), 1178 (m) cm−1; elemental analysis: (theor): C=69.89, H=6.84, (exp): C=69.95, H=6.99. Melting point: 55-56° C.

Provenance & Evidence