Water → 3-Hexanone, 6-nitro-

HRID 400214Notes

Reaction equation

HRID 400214 reaction equation
[CH:1]([C:3]([CH2:5][CH3:6])=[O:4])=[CH2:2].[N+:7]([CH3:10])([O-:9])=[O:8].CN(C)C(N(C)C)=N.O>C(#N)C.C(O)(=O)C>[N+:7]([CH2:10][CH2:2][CH2:1][C:3](=[O:4])[CH2:5][CH3:6])([O-:9])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 153941-Penten-3-oneHCID 664601,1,3,3-Tetramethylguanidine

Product 1

HCID 116439463-Hexanone, 6-nitro-Yield 19.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A! Ethyl vinyl ketone (25 g, 0,297 mole) was slowly added to a solution of nitromethane (80 ml, 1.48 mole) and 1,1,3,3-tetramethylguanidine (3.7 ml, 0.029 mole) in acetonitrile (180 ml) while maintaining the room temperature by cooling with ice. The reaction mixture was stirred for 48 hours at room temperature, then added with water (70 ml), and the pH was corrected to 5 by acetic acid. The solvent was evaporated under vacuum and the aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with chilled water (100 ml) and anhydrified over sodium sulfate, then the solvent was evaporated under vacuum to give 42 g of crude 6-nitrohexan-3-one which was used as such in the next step.

Workup

  1. temperatureby cooling with ice
  2. customThe solvent was evaporated under vacuum
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×100 ml)
  4. washThe combined organic phases were washed with chilled water (100 ml)
  5. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-870842b640db4f11bb89ee7411298fd2
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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