Hydrochloric Acid → alpha-Phenyl[1,1'-biphenyl]-4-methanol

HRID 1111656

Reaction equation

HRID 1111656 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O.Cl>C(O)C>[C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[CH:9][C:10]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[OH:12])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 750404-BenzoylbiphenylHCID 4311764Sodium borohydride

Product 1

HCID 95512alpha-Phenyl[1,1'-biphenyl]-4-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

38.8 g (0.15 mol) of 4-phenylbenzophenone are dissolved in 200 ml of ethanol and 3 g (0.075 mol) of sodium borohydride are added. After heating for 15 hours under reflux, and allowing to cool, the reaction mixture is hydrolyzed with water containing a little hydrochloric acid. The solid thereby produced is purified by recrystallization from ethanol. 36 g (89% of theory) of (biphenyl-4-yl)-phenyl-carbinol [alternatively named as diphenyl-phenyl carbinol or α-(biphenyl-4-yl)benzylalcohol] of melting point 72°-73° C. are obtained.

Workup

  1. temperatureAfter heating for 15 hours
  2. temperatureunder reflux
  3. temperatureto cool
  4. customThe solid thereby produced
  5. customis purified by recrystallization from ethanol
  6. customare obtained

Sources & evidence

ORD record
ord-45182ab4d29b44818040161a2a1e24d8
Source dataset
uspto-grants-1978_10
Patent number
US04118487

Linked notes

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