Cornforth reagent → 3,3-Dimethoxy-2,2-dimethylpropanal

HRID 345210Notes

Reaction equation

HRID 345210 reaction equation
[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:9][CH3:10])[C:4]([CH3:8])([CH3:7])[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 110080703,3-Dimethoxy-2,2-dimethylpropan-1-ol

Product 1

HCID 108988453,3-Dimethoxy-2,2-dimethylpropanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 90 g (0.61mol) of the product of Example 2 and 250mg (0.66 mol) of pyridinium dichromate was stirred rapidly in 2 L of CH2Cl2 for 40 hours. The mixture was filtered through Celite, the filtrate passed through a column of Florisil and the solvent evaporated. Distillation of the residue through a 45 cm vigreux column furnished the title compound as a water-white oil, bp 65°-68°/10 mm, 31.4 g (35%). Calculated for C7H14O3 : C,57.51; H, 9.65. Found: C, 57.69; H, 9.85.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe solvent evaporated
  3. distillationDistillation of the residue through a 45 cm vigreux column

Sources & evidence

ORD record
ord-e44a63fdcfee4b16aacc773dd82c39e3
Source dataset
uspto-grants-1991_10
Patent number
US05055613

Reaction notes

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