Water → HCID 23108397, compound

Participants

Reaction Steps

In 300 ml of toluene was dissolved 30.0 g of methyl 4-hydroxy-4-(2,2-dihydroxy-1,1,3,3,3-pentafluoropropyl)-cyclohexanecarboxylate obtained in <6-1>. The solution was stirred and heated under reflux while the water formed was continuously removed. Under nitrogen atmosphere and with stirring, this solution was added dropwise to a solution of 5.0 g lithium aluminum hydride in 100 ml tetrahydrofuran. The mixture was stirred at 5° C. for one hour and then at room temperature for 18 hours. The reaction mixture was combined with 500 ml of 10% hydrochloric acid and extracted with ethyl acetate. Through conventional work-up including washing, drying and concentration, a crude product was obtained. Recrystallization from n-hexane gave 20.8 g (yield 80%) of the target compound.

Provenance & Evidence