Hydrochloric Acid → HCID 178495618, compound

Participants

Reaction Conditions

Reaction Steps

Into a 500 ml three-neck flask were placed the compound (VI) (21 g, 0.064 mol) obtained at the fourth step and dry toluene (40 ml) in dry nitrogen atmosphere, followed by dissolving with stirring. To the solution was dropwise added a commercially available 1.67N hexane solution (42.7 ml) of n-butyllithium (0.067 mol) over about 10 minutes at a liquid temperature kept at 20° to 25° C. After completion of the addition, the mixture was kept at 25° C. for 30 minutes, and then cooled to 5° C., followed by dropwise adding 4-propylcyclohexanone (11.2 g, 0.08 mol) over 20 minutes while the temperature was kept at 5° to 10° C., further keeping the temperature at 45° C. for 30 minutes, dropwise adding water (20 ml), further dropwise adding 6N-HCl (40 ml) while the temperature was kept at 30° C. or lower, separating off the resulting organic layer, adding potassium hydrogen sulfate (KHSO4) (2 g), distilling off the solvent on heating, concentrating until the liquid temperature reached 110° C., during which dehydration reaction proceeded, cooling, transferring into a separating funnel, washing the resulting organic layer with water, distilling off the solvent, recrystallizing the residue from ethyl alcohol (10 c.c.) to obtain trans-4-methyloxymethyl-1-(4'-methyl-1-cyclohexenylphenyl)cyclohexane (VII) (5.3 g) having a melting point (C-S point) of 64° C., a S-N point of 93.4° C. and a clearing point (N-I point) of 14.3° C.

Provenance & Evidence