Water → 3-Biphenylmethanol

HRID 1961461Notes

Reaction equation

HRID 1961461 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7](O)=[O:8])[CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 6035563-BiphenylmethanolYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Biphenyl-3-carboxylic acid (217.0 mg, 1.09 mmol) in THF was added to LiAlH4 (1.0 M in THF) (1.64 ml) at 0° C. under N2 during 15 min. The mixture was then stirred at r.t. for 2.5 h. H2O was carefully added to the mixture at 0° C. NaOH (1.0 M) was added. The product was extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated yielding the title compound as a yellow oil (95%).

Workup

  1. extractionThe product was extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-41490f03146449d9ab826c8174a6bb30
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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