Water → 2-(4-Methylcyclohex-3-en-1-yl)propane-2-thiol

HRID 1633087Notes

Reaction equation

[S:1]1[CH2:10][C:2]1([CH3:11])[CH:3]1[CH2:8][CH2:7][C:6]([CH3:9])=[CH:5][CH2:4]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>O1CCCC1>[C:6]1([CH3:9])[CH2:7][CH2:8][CH:3]([C:2]([SH:1])([CH3:10])[CH3:11])[CH2:4][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.637 g (3.8 mM) of the compound prepared according to letter (b) above in 12 ml of tetrahydrofuran (THF) were added under nitrogen atmosphere to a stirred boiling suspension of 72 mg (1.9 mM) of LiAlH4 in 3 ml of THF. The reaction mixture was refluxed for 1 further hour, then cooled at 0° C. and the excess of LiAlH4 decomposed by addition of water. The obtained mixture was then extracted with ether (3×) and the organic phase washed with water (3×), dried and evaporated. After fractional distillation of the crude residue, there were obtained 0.450 g (69% yield) of the desired 1-p-menthene-8-thiol, b.p. 40° C./0.133 Pa.

Workup

additionwere added under nitrogen atmosphere to a stirred
temperatureThe reaction mixture was refluxed for 1 further hour
extractionThe obtained mixture was then extracted with ether (3×)
washthe organic phase washed with water (3×)
customdried
customevaporated
distillationAfter fractional distillation of the crude residue

Sources & evidence

ORD record: ord-9a24b791ab7846cdb080a9634dbb1ab5
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04478865

Reaction notes

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