2-Nitropropane → HCID 21529566, compound

HRID 1657673Notes

Reaction equation

HRID 1657673 reaction equation
[Li].[N+:2]([CH:5]([CH3:7])[CH3:6])([O-:4])=[O:3].[CH3:8][C:9]1[CH:10]=[C:11]([C:15](=[O:22])[C:16]([N+]([O-])=O)([CH3:18])[CH3:17])[CH:12]=[CH:13][CH:14]=1>CN(C)P(N(C)C)(N(C)C)=O>[N+:2]([C:5]([CH3:7])([CH3:6])[C:16]([CH3:17])([CH3:18])[C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH3:8])[CH:10]=1)=[O:22])([O-:4])=[O:3]

Participants

5

Reactant 3

HCID 3982-NitropropaneHCID 3028194LithiumHCID 21529565HCID 21529565, compound

Product 1

HCID 21529566HCID 21529566, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

The lithium salt of 2-nitropropane (0.52 mol.) was dissolved in 700 ml. of hexamethylphosphoramide and, while under nitrogen, 62.1 g. (0.3 mol.) of 3'-methyl-α-nitroisobutyrophenone was added. The reaction mixture was stirred 18 hours under fluorescent lighting. The mixture was then diluted with 1400 ml. of water and the aqueous mixture was extracted three times with 800 ml. portions of ether. The combined ether extracts were washed three times with water, dried over magnesium sulfate and the ether removed. The residue was crystallized from hexane to give a 48 percent yield of 3-nitro-2,2,3,3'-tetramethylbutyrophenone: m.p. 50°-51° C.

Workup

  1. additionThe mixture was then diluted with 1400 ml
  2. extractionof water and the aqueous mixture was extracted three times with 800 ml
  3. washThe combined ether extracts were washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. customthe ether removed
  6. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-cf9e0e1d820745308f13a38ffa5c7e6f
Source dataset
uspto-grants-1976_06
Patent number
US03962053

Reaction notes

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