Ammonium Chloride → 1-(Biphenyl-3-yl)ethanol

HRID 2296980Notes

Reaction equation

HRID 2296980 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>CO.O1CCCC1>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 2585681-((1,1'-Biphenyl)-3-yl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 131027561-(Biphenyl-3-yl)ethanolYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.82 g (50 mmol) of 3-acetylbiphenyl in 80 ml of dry methanol and 80 ml of dry tetrahydrofuran was added 3.36 g (80 mmol) of sodium borohydride portionwise with ice-cooling, and the mixture was stirred for 1 hour. To the reaction solution was added 600 ml of an about 5% aqueous solution of ammonium chloride and the mixture was extracted with tert-butyl methyl ether. The organic layer was dried and concentrated to obtain 9.86 g (49.7 mmol) of 3-(1-hydroxyethyl)biphenyl as an oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with tert-butyl methyl ether
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a0dfb3f3c94840a78b9b28446206a0d8
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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