Hydrochloric Acid → HCID 178448086, compound

HRID 1655149Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16](OCC)=[O:17])[CH2:12][CH2:11]1)[CH2:8][CH3:9].C(OCC)(=O)C.Cl>CCOCC.O>[CH2:7]([C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)[CH2:8][CH3:9]

Participants

Conditions

Temperature: 10 °C

Procedure

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. on 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.

Workup

temperatureheat-refluxed for 1 hour
additionAfter the addition
temperaturefurther heat-refluxed for 1 hour
extractionThe resultant mixture was extracted with isopropyl ether
washthe organic layer was successively washed with water, sodium hydroxide aqueous solution and water
dry with materialby drying with magnesium sulfate, distilling-off of the solvent and purification by silica gel column chromatography

Sources & evidence

ORD record: ord-f235851529c44e168d916e5a7aa44b3f
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05250221

Reaction notes

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