Toluene → HCID 86617042, compound

Participants

Reaction Conditions

Reaction Steps

The preparation of diphenylacetyl p-toluenesulfonate. A 100-mL, flask equipped with a magnetic stirring bar and Dean-Stark apparatus was charged with p-toluenesulfonic acid monohydrate (9.51 g, 0.05 mol) and toluene (60 mL). The mixture was refluxed for 2 h to remove water and toluene was distilled off to 10 mL volume at normal pressure. This residue was cooled to 20-25° C. and added dropwise to a stirred solution of diphenylketene (9.7 g, 0.05 mol) in anhydrous diethylether (20 mL) at 0-5° C. over 3-5 min. The orange solution of diphenylketene became slightly yellow; the reaction mixture was stirred for 6 h at 0-5° C. The formed precipitate was filtered under a nitrogen atmosphere, washed with anhydrous diethyl ether (15 mL) and dried in a nitrogen flow giving diphenylacetyl toluenesulphonate (12.3 g, 67%), as off white prisms, m.p. 84-87° C. (decomposition). 1H NMR (CDCl3) δ 2.43 (s, 3H), 5.01 (s, 1H), 7.10-7.16 (m, 4H), 7.24-7.32 (m, 8H), 7.82 (d, J=7.9 Hz, 2H); 13C NMR (CDCl3) δ 21.7, 57.0, 127.8, 128.4, 128.8, 129.0, 129.6, 132.6, 136.2, 146.0, 165.5. Anal. Calcd. for C21H18O4S (366.44): C, 68.83; H, 4.95. Found: C, 68.61; H, 4.89.

Provenance & Evidence