반응 #1166461

반응 방정식

hydrochloric acid

lithium aluminum hydride

ethyl trans-4-n-propylcyclohexylcarboxylate

ethyl acetate

→

trans-4-n-propylcyclohexylmethanol

수율 87.8%

용매

water

ether

ether

반응 조건

후처리

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

실험 절차

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.

출처