1,4-Cyclohexanediol → 4-(Cyclohex-3-enylmethoxy)cyclohexanol

Participants

Reaction Conditions

Reaction Steps

To toluene (500 g) were added 4-chloromethylcyclohexene (0.1 mol), 1,4-cyclohexanediol (0.5 mol), and tetrabutylammonium bromide (0.01 mol), the mixture was raised in temperature to 90° C., and a 5 N NaOH aqueous solution (100 g) was added dropwise thereto, followed by stirring for 5 hours. A toluene solution (toluene layer) was rinsed with water, concentrated, purified by silica gel chromatography, and thereby yielded 13 g of 4-(cyclohex-3-enylmethoxy)cyclohexanol with a purity of 99%.

Provenance & Evidence