反应详情

Benzaldehyde (26.3 g, 0.25 mol) and hexanoic acid anhydride (53.3 g, 0.25 mol) were dissolved in carbontetrachloride (200 ml) under N2 -atrnosphere. Catalytic amounts of sulfuric acid was added and the reaction mixture stirred at room temperature for 1 hr. The reaction mixture was evaporated over night, the residue dissolved in hexane and the solution filtered through a bed of silica. The filtrate was purified on a silica column, eluting with hexane. The evaporated eluate was a colourless oil and the yield was 14.0 g, 18% of the theoretical. 1H- and 13C NMR (CDCl3) d (ppm) rel. to TMS: 7.72 (s, 1H, CH(OC5H11)2), 7.58-7.39 (m, 5H, Ar-H), 2.37 (double t, 4 H, COCH2), 1.64 (m, 4H, COCH2CH2), 1.30 (m, 4H,CH2CH2CH3) and 0.88 (t, 6H, CH3); 171.524 (C=O), 135.688, 129.523, 128.466 and 126.547 (Ar), 89.398 (CH(OC5H11)2), 33.965, 31.030, 24.235 and 22.179 (CH2) and 13.777 (CH3).

1. customThe reaction mixture was evaporated over night
2. dissolutionthe residue dissolved in hexane
3. filtrationthe solution filtered through a bed of silica
4. customThe filtrate was purified on a silica column
5. washeluting with hexane