2-(Benzyloxy)benzaldehyde → Benzenemethanol, 2-(phenylmethoxy)-

HRID 2268798Notes

Reaction equation

HRID 2268798 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[BH4-].[Na+]>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 3447842-(Benzyloxy)benzaldehyde

Product 1

HCID 18811Benzenemethanol, 2-(phenylmethoxy)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 4311764Sodium borohydrideSolvent

Procedure

To a stirring solution of 2-(benzyloxy)benzaldehyde (10 g, 47 mmol) in 100 mL of Ethanol, NaBH4 was added as a solid in small portions. The reaction temperature was controlled with a room temperature water bath. After stirring for 30 minutes, the reaction was quenched by slow addition of 3N HCl. This solution was extracted with EtOAc and the organic portion washed with water, Sat. Na2CO3 and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the benzy alcohol which was used in the next step without further purification.

Workup

  1. customwas controlled with a room temperature
  2. customthe reaction was quenched by slow addition of 3N HCl
  3. extractionThis solution was extracted with EtOAc
  4. washthe organic portion washed with water, Sat. Na2CO3 and brine
  5. dry with materialThe solution was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3abbb2c502914ae0b68a27d93d3b03b8
Source dataset
uspto-grants-2001_12
Patent number
US06329376B1

Reaction notes

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