4-Chloro-alpha-methylstyrene → 4-Chlorocumene

HRID 543869

Reaction equation

HRID 543869 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH3:8])=[CH2:7])=[CH:4][CH:3]=1.[H][H]>[Pt]=O.C(O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 743814-Chloro-alpha-methylstyreneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 174934-ChlorocumeneYield 74%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of p-chloro-α-methylstyrene (15.7 g, 204 mmole), 20 milligrams (mg) platinum oxide, and 20 ml absolute ethanol was shaken on a Paar Hydrogenator for about 8 hours, beginning with an initial hydrogen pressure of 42 pounds-per-square-inch (psi). During this procedure, an additional 14 psi of hydrogen were added to the Hydrogenator reservoir. The mixture was then filtered and the solvent removed by careful distillation at atmospheric pressure. The residual material resulting was distilled using a water aspirator vacuum to yield 12.69 g (74% yield) of p-chlorocumene (bp 69°-74° C.).

Workup

  1. filtrationThe mixture was then filtered
  2. customthe solvent removed by careful distillation at atmospheric pressure
  3. customThe residual material resulting
  4. distillationwas distilled

Sources & evidence

ORD record
ord-bbeb382fa30e424ebb0024583d6546bf
Source dataset
uspto-grants-1984_05
Patent number
US04447542

Linked notes

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