Phenol → 4'-Hydroxy-4-biphenylcarboxylic acid

HRID 845136Notes

Reaction equation

HRID 845136 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(C3C=CC(O)=CC=3)[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].C1(O)C=CC=CC=1>[C].[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 14093482HCID 14093482, compound

Product 1

HCID 3015564'-Hydroxy-4-biphenylcarboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Conditions

Temperature
200 °C

Procedure

Next, 18.7 g (0.060 mole) of the 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid thus obtained, 2.9 g (0.072 mole) of sodium hydroxide, 100.0 g of phenol, and 0.4 g of 5% palladium-carbon catalyst were charged into a 300-ml stainless steel autoclave. After the air within the autoclave was displaced with nitrogen gas, the reaction mixture was heated at 200° C. for 6 hours. After completion of the reaction, the reaction mixture was filtered to separate unreacted phenol therefrom. The filter cake was dissolved in 50 g of a 20% aqueous solution of sodium hydroxide, and the resulting solution was filtered again to recover the catalyst. In order to precipitate the desired product, the filtrate was brought to pH 1 by the addition of diluted hydrochloric acid. The crystals so formed were collected by filtration, washed with water, and then dried to obtain 11.7 g of 4'-hydroxybiphenyl-4-carboxylic acid in the form of white crystals. Liquid-chromatographic analysis revealed that this product had a purity of 93%, and the greater part of the impurities comprised 4-(4'-hydroxyphenyl)cyclohexanecarboxylic acid. On the basis of the amount of 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid used, the yield of 4'-hydroxybiphenyl-4-carboxylic acid as corrected for its purity was 85%.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. customto separate unreacted phenol
  4. dissolutionThe filter cake was dissolved in 50 g of a 20% aqueous solution of sodium hydroxide
  5. filtrationthe resulting solution was filtered again
  6. customto recover the catalyst
  7. customIn order to precipitate the desired product
  8. additionthe filtrate was brought to pH 1 by the addition of diluted hydrochloric acid
  9. customThe crystals so formed
  10. filtrationwere collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-0d163d4133fd46a9a05da9f1e4b8a0f7
Source dataset
uspto-grants-1988_07
Patent number
US04755617

Reaction notes

Loading…