Reacción #1166461

Ecuación de reacción

hydrochloric acid

lithium aluminum hydride

ethyl trans-4-n-propylcyclohexylcarboxylate

ethyl acetate

→

trans-4-n-propylcyclohexylmethanol

Rendimiento 87.8%

Disolventes

water

ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheat-refluxed for 1 hour
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Temperaturafurther heat-refluxed for 1 hour
4. 4
   ExtracciónThe resultant mixture was extracted with isopropyl ether
5. 5
   Lavadothe organic layer was successively washed with water, sodium hydroxide aqueous solution and water
6. 6
   Secadoby drying with magnesium sulfate, distilling-off of the solvent and purification by silica gel column chromatography

Procedimiento

0.73 g (19.1 mmol) of lithium aluminum hydride was added to 30 ml of dry ether, heat-refluxed for 1 hour and cooled to 10° C. in an iced water bath, and a solution of 5 g (25.5 mmol) of ethyl trans-4-n-propylcyclohexylcarboxylate in 30 ml of dry ether was gradually added dropwise thereto. After the addition, the mixture was stirred for 1 hour and further heat-refluxed for 1 hour, followed by treatment with ethyl acetate and with 6N-hydrochloric acid and pouring into 200 ml of iced water. The resultant mixture was extracted with isopropyl ether and the organic layer was successively washed with water, sodium hydroxide aqueous solution and water, followed by drying with magnesium sulfate, distilling-off of the solvent and purification by silica gel column chromatography to obtain 3.5 g of trans-4-n-propylcyclohexylmethanol.

Fuente