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

HRID 1592031Notes

Reaction equation

HRID 1592031 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]([CH:14]=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[CH2:12][OH:13])[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

Procedure

To a cold (ice-water) solution of the title A compound, 3-benzyloxy-4-nitro-benzaldehyde (6.13 g, 23.8 mmol) in methanol (60 mL) is added in portions with stirring sodium borohydride (906 mg, 24 mmol) and the mixture is allowed to warm up to RT overnight. The mixture is evaporated to dryness at aspirator pressure and the residue is triturated with 2N aqueous HCl and extracted 3 times with EtOAc. The organic extracts are washed with brine, dried over anhydrous MgSO4, filtered and evaporated to give 3-benzyloxy-4-nitro-benzyl alcohol which solidifies on standing at RT under vacuum.

Workup

  1. customThe mixture is evaporated to dryness at aspirator pressure
  2. customthe residue is triturated with 2N aqueous HCl
  3. extractionextracted 3 times with EtOAc
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2b7839d99adc4704ba063e5a02de9f25
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

Loading…