反応 #1166461

反応方程式

hydrochloric acid

lithium aluminum hydride

ethyl trans-4-n-propylcyclohexylcarboxylate

ethyl acetate

→

trans-4-n-propylcyclohexylmethanol

収率 87.8%

溶媒

water

ether

ether

反応条件

後処理

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

実験手順

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.

出典