Benzene → (2-Chlorophenyl)diphenylmethanol

HRID 1855868Notes

Reaction equation

HRID 1855868 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](Cl)(Cl)Cl.[OH2:16].[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[OH:16]

Participants

5

Reactant 4

HCID 241Benzene2×HCID 962WaterHCID 16494Benzene, 1-chloro-2-(trichloromethyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 298659(2-Chlorophenyl)diphenylmethanol

Procedure

Into a flask, benzene (380 ml) was charged, and aluminum chloride (88 g) was suspended therein. A solution of o-chlorobenzotrichloride (138 g, 0.6 mole) in benzene (145 ml) was dropwise added thereto over 2 hours while keeping the temperature at 60° C. After the addition was completed, the mixture was refluxed for 2 hours. The reaction mixture was poured into water (600 ml), and the flask was washed with benzene (240 ml) and water (120 ml). The combined mixture was refluxed for 4 hours. The organic layer was separated, washed with water (400 ml), treated with charcoal (6 g) and filtered. Evaporation of the benzene filtrate gave 172.6 g of o-chlorophenyldiphenylmethanol as a crystalline mass. Yield, 97.7%. M.P., 88.5°-91.5° C.

Workup

  1. customat 60° C
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 2 hours
  4. washthe flask was washed with benzene (240 ml) and water (120 ml)
  5. temperatureThe combined mixture was refluxed for 4 hours
  6. customThe organic layer was separated
  7. washwashed with water (400 ml)
  8. additiontreated with charcoal (6 g)
  9. filtrationfiltered
  10. customEvaporation of the benzene filtrate

Sources & evidence

ORD record
ord-8847892dd2684a0f8b0f2a3659b96da3
Source dataset
uspto-grants-1980_08
Patent number
US04216333

Reaction notes

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