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

HRID 2116478Notes

Reaction equation

HRID 2116478 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.[BH4-].[Na+]>CO>[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 2

HCID 3447842-(Benzyloxy)benzaldehydeHCID 4311764Sodium borohydride2×

Product 1

HCID 18811Benzenemethanol, 2-(phenylmethoxy)-Yield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-benzyloxybenzaldehyde (2.0 g) in methanol (20 mL), NaBH4 (356 mg, 9.42 mmol) was added under ice cooling and stirred for 1 hour. After addition of additional NaBH4 (49 mg), the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was concentrated and water was added to the resulting residue, followed by extracting the mixture with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 2-benzyloxybenzyl alcohol (2.1 g) as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added to the resulting residue
  4. extractionby extracting the mixture with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-82b23a52ead1430fbfe155e8828e5dfc
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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