3-(4-Isopropylphenyl)-1-propene → trans-p-Propenylcumene

HRID 1390209

Reaction equation

HRID 1390209 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][CH:5]=1)[CH:2]=[CH2:3]>[Os](Cl)(Cl)Cl>[CH:1](/[C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:8][CH:9]=1)=[CH:2]\[CH3:3]

Participants

3

Reactant 1

HCID 32826653-(4-Isopropylphenyl)-1-propene

Product 1

HCID 12571311trans-p-PropenylcumeneYield 57%

Reagents, catalysts & solvents 1

HCID 83468Osmium chloride (OsCl3)Catalyst

Procedure

A mixture of 5 g. of p-allylcumene and 5 mg. of osmium trichloride is brought to 110° C. for 71/2 hours. After distillation, a fraction weighing 4.2 g. containing (as measured by gas-liquid chromatography) 31% of p-allylcumene, 12% of cis-p-propenylcumene and 57% of trans-p-propenylcumene is obtained. The conversion rate is 74% and the yield is 78.5%, based on the converted p-allylcumene.

Workup

  1. additionA mixture of 5 g
  2. customis brought to 110° C. for 71
  3. custom2 hours
  4. distillationAfter distillation
  5. additioncontaining (as measured by gas-liquid chromatography) 31% of p-allylcumene, 12% of cis-p-propenylcumene

Sources & evidence

ORD record
ord-1ec358aa4da849d28ae68b48b945206f
Source dataset
uspto-grants-1979_02
Patent number
US04138411

Linked notes

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