Water → 4-Methyl-4-nitrovaleraldehyde

HRID 858969Notes

Reaction equation

HRID 858969 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-3263002563024261b732ee84408d6498
Source dataset
uspto-grants-2006_12
Patent number
US07148371B2

Reaction notes

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