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

HRID 1005690Notes

Reaction equation

HRID 1005690 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

In ethanol (100 ml) was dissolved 7.531 g of 2-(3-nitrophenyl)propanal. Under ice-cooling, sodium borohydride (1.9 g) was added thereto, followed by stirring at room temperature for 1 hour. To the mixture was added brine, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The resulting residue 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. temperatureUnder ice-cooling
  2. extractionby extracting with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by silica gel column

Sources & evidence

ORD record
ord-543be03fe5f2456598ae6c2ad0529112
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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