(1,1'-Biphenyl)-3-carboxylic acid → 3-Biphenylmethanol

HRID 234118Notes

Reaction equation

HRID 234118 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16](O)=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[OH:17][CH2:16][C:15]1[CH:14]=[C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 6035563-BiphenylmethanolYield 77.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 100 mg of lithium aluminum hydride in 20 mL of ether was added 500 mg 3-phenylbenzoic acid. The reaction mixture was stirred at room temperature overnight. After any excess lithium aluminum hydride was destroyed with water, the organic layer was washed successively with 25 mL aliquots of dilute hydrochloric acid, dilute sodium hydroxide and brine. The organic phase was dried over anhydrous sodium sulfate and the solvent removed by evaporation under reduced pressure to yield 360 mg of 3-hydroxymethylbiphenyl as a crystalline solid. This material was used in the next step without further purification.

Workup

  1. customAfter any excess lithium aluminum hydride was destroyed with water
  2. washthe organic layer was washed successively with 25 mL aliquots of dilute hydrochloric acid, dilute sodium hydroxide and brine
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-646f6f2096e64e6abfe05b7d07f31e69
Source dataset
uspto-grants-1997_01
Patent number
US05594141

Reaction notes

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