Hydrochloric Acid → 2-(1-trans-Dodecenyl)benzyl alcohol

HRID 568917Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH:21]=[O:22])#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CCOCC.Cl>O1CCCC1>[CH:7](/[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][OH:22])=[CH:8]\[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 0 °C

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

customAfter coming to room temperature
temperaturethe reaction mixture was refluxed for 18 hours
temperatureThe reaction mixture was then cooled to 0° C.
additionice was added
customthe layers were separated
washThe organic layer was washed with water and brine
concentrationThe dried solution was concentrated

Sources & evidence

ORD record: ord-d90bad09e06548438f4fc87612be1bb7
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04730005

Reaction notes

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