3,3,4-Trimethylpentan-1-ol → 3,3,4-Trimethylpentanal

HRID 586142Notes

Reaction equation

HRID 586142 reaction equation
[CH3:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[CH2:3][CH2:4][OH:5].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[CH2:3][CH:4]=[O:5]

Participants

4

Reactant 2

HCID 124253343,3,4-Trimethylpentan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 124253353,3,4-Trimethylpentanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3,4-Trimethylpentanol (1 equiv) is dissolved in CH2Cl2. Pyridinium chlorochromate (1.5 equiv) is added and the resulting mixture is stirred at ambient temperature. The liquid is decanted and concentrated by rotary evaporation. The residue is triturated with 1 to 1 diethyl ether/hexane and mixture is filtered and the filtrate is washed with 1 N HCl. The organic layer is dried over Na2SO4, decanted and concentrated. The aldehyde is purified by fractional distillation to yield 3,3,4-trimethylpentanal.

Workup

  1. customThe liquid is decanted
  2. concentrationconcentrated by rotary evaporation
  3. customThe residue is triturated with 1 to 1 diethyl ether/hexane and mixture
  4. filtrationis filtered
  5. washthe filtrate is washed with 1 N HCl
  6. dry with materialThe organic layer is dried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated
  9. distillationThe aldehyde is purified by fractional distillation

Sources & evidence

ORD record
ord-c4d859fffe7a41c28f5913316149751e
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

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