Hydrochloric Acid → HCID 178444441, compound

Participants

Reaction Steps

A mixture of 1.3 g of lithium aluminium hydride and 100 ml of absolute diethyl ether was placed at 0° C. and while gassing with nitrogen and treated with a solution 10 g of aluminium chloride and 200 ml of absolute diethyl ether. After completion of the addition the mixture was stirred at room temperature for a further 20 minutes and treated within 30 minutes with a solution of 9 g of 1-(trans-4-pentylcyclohexyl)-4-[4-(trans-4-pentylcyclohexyl)butanoyl]benzene and 100 ml of absolute dichloromethane. After completion of the addition the reaction mixture was heated overnight under slight reflux, then cooled to 0° C. and treated with 50 ml of water and 500 ml of 25% hydrochloric acid. The organic phase was separated and the aqueous phase was back-extracted three times witch 100 ml of diethyl ether each time. The combined organic phases were washed with 500 ml of water, 250 ml of concentrated potassium carbonate solution and again with 500 ml of water, dried over magnesium sulfate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with toluene and recrystallization from acetone gave 5.7 g of 1-(trans-4-pentylcyclohexyl)-4-[4-(trans-4-pentylcyclohexyl)-1-butyl]benzene with m.p. (C-SB) 50° C. and cl.p. (SB -I) 111° C.

Provenance & Evidence