Eugenol → Isoeugenol

HRID 1390208

Reaction equation

HRID 1390208 reaction equation
[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)[CH2:7][CH:8]=[CH2:9])[OH:3]>[Os](Cl)(Cl)Cl>[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)/[CH:7]=[CH:8]\[CH3:9])[OH:3].[C:1]1([O:11][CH3:12])[C:2](=[CH:4][CH:5]=[C:6]([CH:10]=1)/[CH:7]=[CH:8]/[CH3:9])[OH:3]

Participants

4

Reactant 1

HCID 3314Eugenol

Product 2

HCID 853433IsoeugenolYield 94.5%HCID 1549041cis-IsoeugenolYield 5.5%

Reagents, catalysts & solvents 1

HCID 83468Osmium chloride (OsCl3)Catalyst

Procedure

A mixture of 20 g. of crude clove oil containing about 80% of eugenol and 50 mg. of osmium trichloride is heated for 41/4 hours to 135° C. After distillation, a fraction weighing 13.3 g. and containing, (as determined by gas-liquid chromatography) 5.5% of cis-isoeugenol and 94.5% of trans-isoeugenol is obtained. The yield is 83%, based on the eugenol originally present in the clove oil.

Workup

  1. additionA mixture of 20 g
  2. distillationAfter distillation
  3. additionand containing

Sources & evidence

ORD record
ord-7cd7cded912840e9a2d1d9103601f19a
Source dataset
uspto-grants-1979_02
Patent number
US04138411

Linked notes

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