Alpha-Methylstyrene → 4,4'-Dihydroxybiphenyl

HRID 2352656Notes

Reaction equation

HRID 2352656 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.CC(C1C=CC=CC=1)=C.[OH-].[Na+]>[C].[Pd].O>[C:2]1([OH:1])[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7407Alpha-MethylstyreneHCID 14798Sodium HydroxideHCID 143657084-(4-Hydroxyphenyl)-3-cyclohexen-1-ol

Product 1

HCID 71124,4'-DihydroxybiphenylYield 99.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

A 300-ml stainless steel autoclave was charged with 38.0 g (0.20 mole) of 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol, 1.5 g of 5% palladium-carbon, 70.9 g (0.60 mole) of α-methylstyrene and 100 g of water, and the internal atmosphere was replaced with nitrogen. The mixture was heated and reacted at 200° C. for 3 hours. The reaction mass was poured into a large volume of an aqueous sodium hydroxide solution, and the insoluble catalyst was removed by filtration. The organic layer was removed from the filtrate. The rest of the filtrate was neutralized to pH 4 by adding an aqueous hydrochloric acid solution. The separated crystals were filtered, washed with water and dried to obtain 37.0 g of 4,4'-biphenol as white crystals. The product had a purity of 98.0% and the yield was 97.4% based on 4-(4-hydroxyphenyl)-3-cyclohexene-1-ol.

Workup

  1. temperatureThe mixture was heated
  2. customreacted at 200° C. for 3 hours
  3. customthe insoluble catalyst was removed by filtration
  4. customThe organic layer was removed from the filtrate
  5. additionby adding an aqueous hydrochloric acid solution
  6. filtrationThe separated crystals were filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-ffe682693106477498bd594c5e38e948
Source dataset
uspto-grants-1989_10
Patent number
US04877907

Reaction notes

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