Water → 4-Methyl-4-nitrovaleraldehyde

HRID 433001Notes

Reaction equation

HRID 433001 reaction equation
[CH3:1][C:2]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:3][CH2:4][C:5]#N.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.O.S([O-])([O-])(=O)=[O:29].[Mg+2]>C(Cl)Cl>[CH3:1][C:2]([N+:8]([O-:10])=[O:9])([CH3:7])[CH2:3][CH2:4][CH:5]=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 38791404-Methyl-4-nitrovaleronitrileHCID 21273587HCID 21273587, compound

Product 1

HCID 122640094-Methyl-4-nitrovaleraldehydeYield 369.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methyl-4-nitrovaleronitrile (10.4 g, 13 mmol) was dissolved in methylene chloride (100 ml) and 1M diisobutyl aluminum hydride-hexane solution (100 ml) was added dropwise at −50° C. The mixture was stirred for 0.5 h, and water (8 ml) was added gradually, after which magnesium sulfate (5.0 g) was added. The mixture was filtrated and 1N hydrochloric acid (50 ml) was added. The mixture was stirred for 0.5 h and the layers were separated. The organic layer was washed with saturated brine and the solvent was evaporated. The residue was dried to give oily 4-methyl-4-nitropentanal (6.9 g, 48 mmol).

Workup

  1. filtrationThe mixture was filtrated
  2. addition1N hydrochloric acid (50 ml) was added
  3. stirringThe mixture was stirred for 0.5 h
  4. customthe layers were separated
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe residue was dried

Sources & evidence

ORD record
ord-463a1bcf2b5c4c508ce567decfdc0ea9
Source dataset
uspto-grants-2003_12
Patent number
US06664412B2

Reaction notes

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