Benzaldehyde → 2-Nitro-1-phenyl-1-propanol

HRID 2359934Notes

Reaction equation

HRID 2359934 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([CH2:12][CH3:13])([O-:11])=[O:10].O>O1CCCC1.C(O)(C)(C)C.CC(C)([O-])C.[K+]>[N+:9]([CH:12]([CH3:13])[CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:8])([O-:11])=[O:10]

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 6587Nitroethane

Product 1

HCID 2261182-Nitro-1-phenyl-1-propanolYield 93.7%

Reagents, catalysts & solvents 3

HCID 23665647Potassium tert-butoxideCatalystHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzaldehyde (20.0 g) and nitroethane (28.4 g) in tetrahydrofuran (50 mL) and tert-butanol (50 mL) was added potassium tert-butoxide (1.27 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1) to give the title compound as a blue oil (yield 32.0 g, 93%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1)

Sources & evidence

ORD record
ord-783b2d95b9454079a030f2ed08c28513
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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