1,2-Dichloro-4-isopropenylbenzene → 3,4-Dichlorocumene

HRID 543872Notes

Reaction equation

HRID 543872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([CH3:7])=[CH2:6].[H][H]>[Pt]=O.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]([CH3:7])[CH3:6])[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

5

Reactant 2

HCID 6042561,2-Dichloro-4-isopropenylbenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 749543,4-DichlorocumeneYield 95%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

3,4-dichloro-α-methylstyrene (21.9 g, 118 mmole), approximately 100 mg platinum oxide, and 125 ml absolute ethanol were shaken on a Paar Hydrogenator for four hours, at an initial hydrogen pressure of 50 psi. The material was then filtered through celite, and the solvent removed by distillation at atmospheric pressure. The resulting residual material was distilled at reduced pressure to produce 19.9 g (95% yield) of 3,4-dichlorocumene, bp 123°-126° C.

Workup

  1. filtrationThe material was then filtered through celite
  2. customthe solvent removed by distillation at atmospheric pressure
  3. distillationThe resulting residual material was distilled at reduced pressure

Sources & evidence

ORD record
ord-709f56e6936440a6b034bf55716f6767
Source dataset
uspto-grants-1984_05
Patent number
US04447542

Reaction notes

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