Sodium borohydride → 2-(3-Nitrophenyl)propan-1-ol

HRID 1173133Notes

Reaction equation

HRID 1173133 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[CH:11]=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[BH4-].[Na+]>C(O)C.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]([CH3:13])[CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 226741372-(3-Nitrophenyl)propanal

Product 1

HCID 226740402-(3-Nitrophenyl)propan-1-olYield 82.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-(3-Nitrophenyl)propanal (7.531 g) was dissolved in ethanol (100 ml), to which was then added sodium borohydride (1.9 g) under ice-cooling, followed by stirring at room temperature for one hour. Brine was added thereto, followed by extracting with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. A residue obtained by evaporating the solvent was purified by silica gel column, to give the title compound (6.275 g, 57.19% in 3 steps) as a brown oil.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customA residue obtained
  5. customby evaporating the solvent
  6. customwas purified by silica gel column

Sources & evidence

ORD record
ord-ad3602dcf0034d8c92c6970e9efe97e1
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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