Pyrolytic Chemistry of Benzyl Benzoate

Abstract

Flash vacuum pyrolysis of benzyl beazoate (3) at temperatures in the range 750-900'C and at 10. 2 torr gave diphcnylmethane (5) as the major product with toluene (6) and eight other trace products. namely biphenyl (7), dibenzyl (8),2-, 3-, 4-phenyltoluenes (9, )(), 11, respectively), fluorene (12), benzyl alcohol (4) and benzaldehyde (13). The mechanism or formation of these products is proposed to involve benzyl and phenyl radicals.

Direct Transacylation of 2,2,2-Trihaloethyl Esters with Amines and Alcohols Using Phosphorus(III) Reagents for Reductive Fragmentation and in Situ Activation

“…Benzyl Benzoate (10c). Ester 10c was obtained in 77% yield (40.3 mg) from 2a and benzyl alcohol as a colorless oil (flash chromatography 1.5% EtOAc in hexanes). Data for 10c : R f 0.58 (20% EtOAc in hexanes); IR (thin film) 3063, 3033, 1719, 1271, 1109, 711 cm -1 ; 1 H NMR (CDCl 3 , 300 MHz) δ 8.08 (m, 2H), 7.54 (tt, 1H, J = 7.3, 1.3 Hz), 7.47−7.30 (m, 7H), 5.36 (s, 2H); 13 C NMR (CDCl 3 , 75 MHz) δ 166.4 (C), 136.0 (C), 133.0 (CH), 130.1 (C), 129.7 (CH × 2), 128.5 (CH × 2), 128.3 (CH × 2), 128.2 (CH), 128.1 (CH × 2), 66.6 (CH 2 ); MS (EI) m / e (relative intensity, assignment) 212.1 (39.6, M + ), 105.0 (100, C 6 H 5 CO + ), 91.0 (55.4, C 6 H 5 CH 2 + ), 77.0 (34.6, C 6 H 5 + ).…”