Phenacyl bromide → alpha-Hydroxyacetophenone

Participants

Reaction Conditions

Reaction Steps

This procedure was adapted from the one developed by Pirkle and Simmons (Pirkle, W. H. and Simmons, K A., J. Org. Chem. 48:2520-2527 (1983)). 11.62 g (0.1706 moles) sodium formate was stirred in 50 ml ethanol for about 15 minutes. 5.31 g (26.7 mmol) phenacyl bromide was added to it and the mixture was refluxed under nitrogen at 105° C. for nearly 20 h. The reaction mixture was cooled and complete conversion of the starting material was confirmed by TLC. The solvent was evaporated and about 50 ml of boiling water was added and the solution was filtered hot. The filtrate was then cooled to precipitate out the alcohol. Yield 3.11 g (86%) from 5.31 g phenacyl bromide, white crystalline solid: mp 82-84° C. (lit. mp 84-85° C. (Pirkle, W. H. and Simmons, K A., J. Org. Chem. 48:2520-2527 (1983)); 1H NMR (CDCl3) δ6 3.49 (t, J=4.5), 4.87 (d, J=4.5), 7.44-7.65 (m, 3H), 7.91 (dd, J1=8, J21.3, 2H); 13C NMR (CDCl3) δ198.4, 134.3, 133.5, 129.0, 127.7, 65.5; EI-MS, m/z (rel. intensity) 136 (M+, 6), 105 (100), 77 (81), 52 (29).

Provenance & Evidence