Sodium borohydride → 3-Benzyloxy-4-nitro-benzyl alcohol

HRID 1642635Notes

Reaction equation

HRID 1642635 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH:12]=[O:13])[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:10]=[C:11]([CH2:12][OH:13])[CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 121117193-(Benzyloxy)-4-nitrobenzaldehyde

Product 1

HCID 545187813-Benzyloxy-4-nitro-benzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Benzyloxy-4-nitrobenzaldehyde (10.3 g, 0.040 mol) is dissolved in methanol (120 mL) with heating and then cooled to 0° C. To this stirred solution, sodium borohydride (1.5 g, 0.40 mol) is added in portions over a period of 5 min. The mixture is allowed to warm to ambient temperature and stirred overnight. The solvent is removed under reduced pressure and EtOAc is added. The organic layer is washed with 1N HCl and brine, dried over sodium sulfate/magnesium sulfate, and concentrated to afford (3-benzyloxy-4-nitrophenyl) -methanol as a yellow-brown solid: MS (M+NH4)+=277.

Workup

  1. temperaturewith heating
  2. temperatureto warm to ambient temperature
  3. customThe solvent is removed under reduced pressure and EtOAc
  4. additionis added
  5. washThe organic layer is washed with 1N HCl and brine
  6. dry with materialdried over sodium sulfate/magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c1c6ae0f17f54711bd8a812c4cbe1d0f
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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