Dichloromethane → Propanal, 3-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-

HRID 1284846Notes

Reaction equation

HRID 1284846 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(Cl)Cl.[CH3:25][C:26]([CH3:40])([CH2:29][O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)[CH2:27][OH:28]>C(OCC)C>[CH3:25][C:26]([CH3:40])([CH2:29][O:30][CH2:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1)[CH:27]=[O:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724130Cornforth reagentHCID 109661562,2-Dimethyl-3-(4-methoxyphenylmethoxy)propanol

Product 1

HCID 11085390Propanal, 3-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a dry three-neck flask equipped with a mechanical stirrer and an addition funnel was placed 110 g of pyridinium dichromate and 200 ml of dry CH2Cl2. The mixture was stirred vigorously and then 42 g of 2,2-dimethyl-3-(4-methoxyphenylmethoxy)propanol, the product of Example 5a, was added in one portion. The resulting reaction mixture was stirred for 4 hours. The black brown mixture was poured into 400 ml ethyl ether and the mixture was filtered through a dry silica gel column to obtain a colorless solution. Removal of the solvent gave a residue which was distilled through a vigreux column to obtain the title compound, bp 83°-100°/0.25 mm Hg.

Workup

  1. customIn a dry three-neck flask equipped with a mechanical stirrer and an addition funnel
  2. customThe resulting reaction mixture
  3. stirringwas stirred for 4 hours
  4. filtrationthe mixture was filtered through a dry silica gel column
  5. customto obtain a colorless solution
  6. customRemoval of the solvent
  7. customgave a residue which
  8. distillationwas distilled through a vigreux column

Sources & evidence

ORD record
ord-4c515276975e4f108d1e0d3452eddcbe
Source dataset
uspto-grants-1986_01
Patent number
US04564476

Reaction notes

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