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

HRID 660547Notes

Reaction equation

HRID 660547 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 RT and stirred for 18 h. 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 the title compound as a yellow-brown solid: (M+NH4)+=277.

Workup

  1. temperaturewith heating
  2. temperatureto warm to RT
  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-11676f4489a841f4ba7893945e808882
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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