4-benzyl-2-cyclohexen-1-one → 4-Benzylcyclohex-2-en-1-ol

HRID 1737170Notes

Reaction equation

HRID 1737170 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[CH2:7]([CH:14]1[CH2:19][CH2:18][CH:17]([OH:20])[CH:16]=[CH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 117692464-benzyl-2-cyclohexen-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 150742504-Benzylcyclohex-2-en-1-olYield 98.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 3.2 g of lithium aluminum hydride in 500 ml of ether, 30 g of 4-benzyl-2-cyclohexen-1-one were added dropwise at 0° C. After stirring the mixture for 2 hours at the same temperature, it was washed with diluted hydrochloric acid and water, and the resultant organic layer was dried and concentrated, thereby obtaining 31 g of a crude product. This product was purified by column chromatography to obtain 30 g (yield: 98%) of 4-benzyl-2-cyclohexen-1-ol. A ratio of a cis-form to a trans-form was found to be 32:68 by 1H-NMR.

Workup

  1. additionwere added dropwise at 0° C
  2. washwas washed with diluted hydrochloric acid and water
  3. customthe resultant organic layer was dried
  4. concentrationconcentrated
  5. customobtaining 31 g of a crude product
  6. customThis product was purified by column chromatography

Sources & evidence

ORD record
ord-395b1e6357254a21ad13264f5dcb8043
Source dataset
uspto-grants-1999_10
Patent number
US05962403

Reaction notes

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