3-Hexenol → 3-Hexenal, (3Z)-

HRID 1733357Notes

Reaction equation

HRID 1733357 reaction equation
[CH2:1]([OH:7])[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6]>C(Cl)Cl>[CH:1](=[O:7])[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6].[CH2:1]([OH:7])[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH3:6]

Participants

4

Reactant 1

HCID 52811673-Hexenol

Product 2

HCID 6439413-Hexenal, (3Z)-Yield 31.3%HCID 52811673-HexenolYield 19.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 Grams (0.1 moles) of cis-3-hexenol and 20 ml methylene chloride are then added rapidly over a 2 minute period. The reaction mixture is then stirred for a period of 15 minutes during which time the temperature is allowed to rise reaching a maximum of 40° C. The resulting liquid is decanted and the residue is washed with diethylether. The combined organic layers are then filtered through silica gel on a sintered glass funnel, dried and concentrated. The GLC profile indicates 61.0% cis-3-hexenal and 29.5% of cis-3-hexenol. Removal of most of the solvent yields 6.14 grams of which 31.3% of cis-3-hexenal and 19.4% of cis-3-hexenol.

Workup

  1. customa maximum of 40° C
  2. customThe resulting liquid is decanted
  3. washthe residue is washed with diethylether
  4. filtrationThe combined organic layers are then filtered through silica gel on a sintered glass funnel
  5. customdried
  6. concentrationconcentrated
  7. customRemoval of most of the solvent

Sources & evidence

ORD record
ord-10ff449a8c334a18b9a8c671318c3248
Source dataset
uspto-grants-1980_12
Patent number
US04241098

Reaction notes

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