2-(1-trans-Dodecenyl)benzyl alcohol → 2-(1-trans-Dodecenyl)benzaldehyde

HRID 568918Notes

Reaction equation

HRID 568918 reaction equation
[CH:1](/[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][OH:16])=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH:1](/[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16])=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 1

HCID 703770362-(1-trans-Dodecenyl)benzyl alcohol

Product 1

HCID 159265662-(1-trans-Dodecenyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of lithium aluminum hydride (22.2 mmoles) in tetrahydrofuran (30 ml) under argon, cooled to 0° C., was added 2-(1-dodecyn-1-yl) benzaldehyde (11.1 mmoles, prepared as in Example 4(a) in tetrahydrofuran (10 ml), dropwise with stirring. After coming to room temperature, the reaction mixture was refluxed for 18 hours. The reaction mixture was then cooled to 0° C., ice was added, followed by ether and dilute hydrochloric acid, and the layers were separated. The organic layer was washed with water and brine. The dried solution was concentrated to give 2-(1-trans-dodecenyl)benzyl alcohol, after recrystallization from acetonitrile. The benzyl alcohol (0.080 mmoles) was dissolved in ethyl acetate (10 ml) under argon and manganese dioxide (12.6 mmoles) was added. The reaction mixture was stirred for 18 hours at room temperature, filtered and the filtrate concentrated to leave an oil which is the desired product.

Workup

  1. customafter recrystallization from acetonitrile
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. customto leave an oil which

Sources & evidence

ORD record
ord-852784e9ad154934af624b034e489041
Source dataset
uspto-grants-1988_03
Patent number
US04730005

Reaction notes

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