Phenol → 4-(1-Phenylcyclohexyl)phenol

HRID 237749

Reaction equation

HRID 237749 reaction equation
[C:1]1([C:7]2(O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>[C:1]1([C:7]2([C:17]3[CH:18]=[CH:19][C:14]([OH:20])=[CH:15][CH:16]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 153191-Phenylcyclohexanol

Product 1

HCID 15384544-(1-Phenylcyclohexyl)phenolYield 78.9%

Reagents, catalysts & solvents 2

HCID 124969952-Methylbenzenesulfonic acid hydrateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5 g (28.4 mmol) of 1-phenyl-1-cyclohexanol, 5.35 g (56.8 mmol) of phenol and 250 mg (1.32 mmol) of toluenesulfonic acid monohydrate was stirred at 85° C. under nitrogen atmosphere for 4 hours. The material was allowed to cool to room temperature, diluted with ethyl acetate, washed with saturated sodium bicarbonate, water and brine. The resulting solution was dried (Na2SO4), filtered and concentrated to a white solid which was heated under high vacuum to remove residual phenol. The resulting residue was purified by flash chromatography on silica gel, eluting with methanol/dichloromethane to provide 5.64 g (22.4 mmol) of 4-(1′-(phenyl)cyclohexyl)phenol.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with saturated sodium bicarbonate, water and brine
  3. dry with materialThe resulting solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a white solid which
  6. temperaturewas heated under high vacuum
  7. customto remove residual phenol
  8. customThe resulting residue was purified by flash chromatography on silica gel
  9. washeluting with methanol/dichloromethane

Sources & evidence

ORD record
ord-03f4c38d3ae34542b0c677855a714989
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Linked notes

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