Ammonium Chloride → 3-(1-(Benzyloxyimino)ethyl)benzylalcohol

HRID 2296969Notes

Reaction equation

HRID 2296969 reaction equation
[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.O1CCCC1>[CH2:1]([O:8][N:9]=[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][OH:16])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×HCID 734333173-(1-(Benzyloxyimino)ethyl)benzaldehyde

Product 1

HCID 867586303-(1-(Benzyloxyimino)ethyl)benzylalcoholYield 96.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.92 g (39.17 mmol) of 3-(1-(benzyloxyimino)ethyl)benzaldehyde in 70 ml of dry methanol and 70 ml of dry tetrahydrofuran was added 1.81 g (43 mmol) of sodium borohydride portionwise with ice-cooling, and the mixture was stirred for 2 hours with ice-cooling. Further, 0.30 g of sodium borohydride portionwise was added thereto with ice-cooling, and the mixture was stirred for 2 hours with ice-cooling. The reaction mixture was poured into 500 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 9.64 g (37.8 mmol) of 3-(1-(benzyloxyimino)ethyl)benzylalcohol.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturewith ice-cooling
  4. stirringthe mixture was stirred for 2 hours with ice-
  5. temperaturecooling
  6. extractionthe mixture was extracted with tert-butyl methyl ether
  7. customThe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-565bdc0af0c14cd8850cc433c1c28e52
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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