Hydrochloric Acid → 4,4'-(4-Phenylcyclohexylidene)bisphenol

HRID 1647355Notes

Reaction equation

HRID 1647355 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Ca+2].[Cl-].Cl.C([O:27][CH2:28][CH3:29])(=O)C>O>[OH:19][C:13]1[CH:18]=[CH:17][C:16]([C:4]2([C:1]3[CH:6]=[CH:29][C:28]([OH:27])=[CH:3][CH:2]=3)[CH2:5][CH2:6][CH:1]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:2][CH2:3]2)=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 8857Ethyl AcetateHCID 13229CyclohexylbenzeneHCID 5284359Calcium Chloride

Product 1

HCID 152791364,4'-(4-Phenylcyclohexylidene)bisphenol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 51.6 g of 4-phenylcyclohexane, 111.5 g of phenol and 65.7 g of calcium chloride, 24.7 ml of concentrated hydrochloric acid was slowly added dropwise by vigorous stirring of the mixture at room temperature. Then, the mixture was stirred for eight hours and left for more than 168 hours at room temperature. 0.3 liters of warm water and one liter of ethyl acetate were added to the mixture to dissolve by heating, and the mixture was washed with a saturated sodium chloride solution (warm water of 40°-50° C. was used). After drying with MgSO4, the mixture was filtered and concentrated. The resultant concentrate was recrystallized with toluene to obtain 64.9 g of white 1,1-bis(4-hydroxyphenyl)-4-phenylcyclohexane. The melting point was 262.1°-263.3° C.

Workup

  1. additionwas slowly added dropwise
  2. stirringThen, the mixture was stirred for eight hours
  3. waitleft for more than 168 hours at room temperature
  4. dissolutionto dissolve
  5. temperatureby heating
  6. washthe mixture was washed with a saturated sodium chloride solution (warm water of 40°-50° C. was used)
  7. dry with materialAfter drying with MgSO4
  8. filtrationthe mixture was filtered
  9. concentrationconcentrated
  10. concentrationThe resultant concentrate
  11. customwas recrystallized with toluene

Sources & evidence

ORD record
ord-b54fa0ddb77a4770bea78d8517db6aa9
Source dataset
uspto-grants-1995_07
Patent number
US05430195

Reaction notes

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