Hydrochloric Acid → Biphenyl phenyl-carbinol

HRID 643174

Reaction equation

HRID 643174 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][C:10]([C:11](C3C=CC=CC=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:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:19][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]1([CH2:11][OH:12])[CH:19]=[CH:20][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 750404-Benzoylbiphenyl3×HCID 4311764Sodium borohydride

Product 1

HCID 21946058Biphenyl phenyl-carbinol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The method of synthesis presented in Ger.Pat. 2,461,406 uses 4-phenylbenzophenone as partition reactant, and has 2 or three steps, depending on the variation of synthesis to use. One of the variations comprises the dissolution of 4-phenylbenzophenone in ethanol, then adding sodium borohydride in a 1:2 molar relation to 4-phenyl benzophenone, for the reduction of ketone to alcohol. The system is heated to reflux during fifteen hours, it is let to cool down and the reaction mixture is hydrolyzed with water acidulated with HCl, the solid obtained is purified by recrystallization in ethanol. 89% of the theoretical yield of biphenyl-phenyl-carbinol is obtained.

Workup

  1. customThe method of synthesis
  2. customas partition reactant
  3. customdepending on the variation of synthesis
  4. temperatureThe system is heated
  5. temperatureto reflux during fifteen hours
  6. temperatureto cool down
  7. customthe solid obtained
  8. customis purified by recrystallization in ethanol

Sources & evidence

ORD record
ord-7e3b4d000d2c4f6a91de8c56827ba920
Source dataset
uspto-grants-2010_04
Patent number
USRE041254E1

Linked notes

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