Cyclohexanone, 4-(4-chlorophenyl)-

1409956-58-6

14472-80-1

1409956-62-2

529-34-0

The general procedure for the synthesis of 4-(4-chlorophenyl)cyclohexanone, compound (CAS:1409956-62-2) and 1-tetrahydronaphthalenone from compound (CAS:1409956-58-6) was as follows: 2-(4-(4-chlorophenyl)-1-hydroxycyclohexyl)-3,4-dihydronaphthalen-1-(2H)-one (12.0 g, 0.034 mol) was added to a reactor equipped with an overhead stirrer and reflux condenser with a heating jacket. Toluene (200 mL) was added to suspend the feedstock, followed by the addition of p-toluenesulfonic acid (0.3 g, 2.5 mol%) to the reaction mixture. The reaction mixture was heated to 60°C and stirred for 6 h. The reaction progress was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure to give a residue. Ethyl acetate (150 mL) was added to the residue and washed with saturated aqueous sodium bicarbonate (NaHCO3). After separation of the organic layer, the solvent was evaporated to give the crude product. The crude product was purified by recrystallization from methanol to give a white solid compound (5.3 g, 50% yield). Gas chromatographic (GC) analysis of the mother liquor obtained after recrystallization showed that α-tetralone and 4-(4-chlorophenyl)cyclohexanone were present in an approximately 1:1 ratio (based on the corresponding retention times and area percentage profiles in the mother liquor) in 50% total yield. gC retention time: α-tetralone (XII): 17.21 min (area percentage: 46).