Nitrogen → 4-Vinylcyclohexylcarbinol

Participants

Reaction Steps

A 1 liter three-necked flask, equipped with thermometer, stirrer and N2 protection, was used. 46.2 g of 4-vinylcyclohexyl formic acid methyl ester and 140 ml of toluene were added to obtain a pale yellow solution. The temperature was decreased with an ice-water bath. A solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene in an amount of 1.2 times higher than the theory amount was added dropwise, and the temperature was controlled to be less than 30° C. After the completion of addition, the temperature was controlled to be at 30° C., and kept at that temperature for 2 hours. The mixture was poured into 220 g of an aqueous solution of 20% NaOH, the temperature was controlled to be less than 30° C., and stirred for half an hour. The organic phase was separated out, the aqueous phase was extracted twice with 300 ml of THF, the organic phases were combined, and the solvent was removed by a rotary evaporator, to obtain 42.1 g of pale yellow liquid. GC purity: 94.4%, wherein cis 38.0%, and trans 56.4%.

Provenance & Evidence