2-Methylstyrene → Cumene

HRID 2352657Notes

Reaction equation

HRID 2352657 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13]CC(O)C[CH:9]=2)=[CH:4][CH:3]=1.[CH3:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=C>[C].[Pd].C(C(CCCC)CO)C>[CH2:16]([CH:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][OH:1])[CH3:15].[CH3:13][C:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)=[CH2:9].[C:5]1([CH:8]([CH3:13])[CH3:9])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

7

Reactant 2

HCID 119042-MethylstyreneHCID 143657084-(4-Hydroxyphenyl)-3-cyclohexen-1-ol

Product 3

HCID 7406CumeneHCID 7407Alpha-MethylstyreneHCID 77202-Ethylhexanol

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 77202-EthylhexanolSolvent

Procedure

A 300-ml four-necked glass flask was charged with 38.0 g (0.20 mole) of 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol, 0.4 g of 5% palladium carbon, 59.1 g (0.50 mole) of o-methylstyrene and 100 ml of 2-ethylhexanol. The mixture was reacted at 160° C. for 4 hours in a nitrogen atmosphere. The reaction mixture was hot filtered at 150° C. to recover the palladium-carbon. 2-Ethylhexanol, α-methylstyrene and cumene formed were distilled off from the filtrate under reduced pressure. 37.2 g of white crystals of 4,4'-biphenol were obtained. The product had a purity of 98.6% based on liquid chromatography, a p-phenylphenol content of 0.9% and a yield converted to a purity basis of 98.5%.

Workup

  1. customThe mixture was reacted at 160° C. for 4 hours in a nitrogen atmosphere
  2. filtrationThe reaction mixture was hot filtered at 150° C.
  3. customto recover the palladium-carbon

Sources & evidence

ORD record
ord-5269662ba705404d9930275307af8aff
Source dataset
uspto-grants-1989_10
Patent number
US04877907

Reaction notes

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