Abstract
The aldol condensation of acetophenone with benzaldehyde was carried out at room temperature under phase transfer conditions using dichloromethane and 40% aqueous sodium hydroxide as solvents and benzyltriethylammonium chloride as a catalyst. A new six-membered carbon ring compound, 2, 4-dibenzoyl-1, 3, 5-triphenylcyclohexanol (4) was obtained in a moderate yield. When benzylideneacetophenone was subjected to the same phase transfer conditions, the same cyclic compound was obtained together with benzaldehyde. Based on these results a plausible mechanism has been proposed in which benzylideneacetophenone is an intermediate product. In addition, treatment of (4) with lithium aluminium hydride in boiling tetrahydrofuran and with concentrated sulfuric acid afforded 2, 4-bis (α-hydroxybenzyl) -1, 3, 5-triphenylcyclohexanol and 4, 6-dibenzoyl-1, 3, 5-triphenylcyclohexene, respectively.
