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

HRID 2395045Notes

Reaction equation

HRID 2395045 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+]>C(O)C>[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 borohydride

Product 1

HCID 18811Benzenemethanol, 2-(phenylmethoxy)-Yield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-benzyloxybenzaldehyde (5 g, Apin) and sodium borohydride (1.4 g) in ethanol (50 ml) was stirred under argon for 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate and added dropwise to 0.1M hydrochloric acid solution (200 ml) at 0° C. The organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxybenzyl alcohol (4.91 g) as an oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. additionadded dropwise to 0.1M hydrochloric acid solution (200 ml) at 0° C
  4. washThe organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml)
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-85d1a19d506641819dae26ff25d4a496
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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