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

HRID 1077677Notes

Reaction equation

HRID 1077677 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

(1st step): 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 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. dissolutionto dissolve
  4. temperatureby heating
  5. washthe mixture was washed with a saturated sodium chloride solution (warm water of 40°-50° C. was used)
  6. dry with materialAfter drying with MgSO4
  7. filtrationthe mixture was filtered
  8. concentrationconcentrated
  9. concentrationThe resultant concentrate
  10. customwas recrystallized with toluene

Sources & evidence

ORD record
ord-ec72d415c1574c6692a536f62fab4935
Source dataset
uspto-grants-1996_08
Patent number
US05545444

Reaction notes

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