Ammonium Chloride → 3-Biphenylmethanol

HRID 2296963Notes

Reaction equation

HRID 2296963 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.O1CCCC1>[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][OH:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 1210533-PhenylbenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 6035563-BiphenylmethanolYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.47 g (30 mmol) of 3-phenylbenzaldehyde in 50 ml of dry methanol and 50 ml of dry tetrahydrofuran was added 1.34 g (32 mmol) of sodium borohydride portionwise with ice-cooling, and further the mixture was stirred for 1 hour with ice-cooling. The reaction mixture was added to 400 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 5.57 g (30 mmol) of 3-phenylbenzylalcohol.

Workup

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

Sources & evidence

ORD record
ord-f368359797f24fff8db69116d0460cbb
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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