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4-(Trans-4-n-propylcyclohexyl)benzaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium bicarbonate; diisobutylaluminium hydride; In methanol; nitrogen; water; toluene;
(i) Preparation of 4-(trans-4-propylcyclohexyl)-benzaldehyde A mixture of trans-4-propyl-(4-cyanophenyl)cyclohexane (100 g, 0.44 mol) and dried toluene (200 ml) was purged with nitrogen gas at 0 C. with stirring, followed by gradually adding a 25 wt. % toluene solution (300g) of diisobutylaluminum hydride in a nitrogen gas current at a reaction temperature of 5 C. or lower, with stirring, gradually raising the reaction temperature up to 20 C. over 3 hours, agitating the resulting mixture at 20 C. for 10 hours in a nitrogen gas current, cooling the reaction mixture down to 0 C., dropwise adding methanol (200 ml), water (200 ml) and further 6N-hydrochloric acid (500 ml) with stirring, adding toluene (300 ml) to the reaction mixture to extract the reaction product, washing the toluene solution five times with a saturated aqueous solution (200 ml) of sodium hydrogen carbonate and further washing with water till the washing liquid became neutral, drying the resulting toluene solution over anhydrous sodium sulfate, filtering off the drying agent, distilling off toluene and distilling the residue under reduced pressure (160 C., 2 mmHg) to obtain the objective product (89 g, 0.39 mol).