Alpha-Methylstyrene → Cumene

HRID 2351802Notes

Reaction equation

HRID 2351802 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[CH2:10]([CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:13][OH:14])[CH3:11]>[C].[Pd]>[CH2:10]([CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:13][OH:14])[CH3:11].[CH3:3][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:1].[C:4]1([CH:2]([CH3:3])[CH3:1])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 7407Alpha-MethylstyreneHCID 77202-Ethylhexanol

Product 3

HCID 7406CumeneHCID 7407Alpha-MethylstyreneHCID 77202-Ethylhexanol

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

In the next step, a stainless steel autoclave was charged with the total amount of the above wet cake, 0.35 g of 5% palladium-carbon, 5.9 g of α-methylstyrene and 100 ml of 2-ethylhexanol and the internal atmosphere was replaced with nitrogen gas. The mixture was reacted at 180° C. for 3 hours, then cooled to 150° C. and filtered to recover the insoluble catalyst. 2-Ethylhexanol, α-methylstyrene and cumene formed by the reaction were distilled off from the filtrate under reduced pressure to obtain 33.6 g of 4,4'-biphenol as white crystals. The product had a purity of 98.2% based on liquid chromatography and contained 1.2% of p-phenylphenol as impurities. The yield of 4,4'-biphenol converted to a purity basis was 89% based on 4,4-bis(4-hydroxyphenyl)cyclohexanol.

Workup

  1. customThe mixture was reacted at 180° C. for 3 hours
  2. filtrationfiltered
  3. customto recover the insoluble catalyst

Sources & evidence

ORD record
ord-f9a1fc8dcf9e48cb98b1a7abcd04cea9
Source dataset
uspto-grants-1989_10
Patent number
US04873374

Reaction notes

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