Phosphorus oxychloride → 4-Methoxy-3-butyl-2,6-dimethyl-benzaldehyde

HRID 371546Notes

Reaction equation

HRID 371546 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[O:18][CH3:19])[CH2:7][CH2:8][CH3:9].[C:20]([O-])(=[O:22])C.[Na+]>CN(C)C=O>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([CH3:17])[C:14]([CH:20]=[O:22])=[C:15]([CH3:16])[C:10]=1[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 202100342-Butyl-3,5-dimethylanisole

Product 1

HCID 202100394-Methoxy-3-butyl-2,6-dimethyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.5 ml. of phosphorous oxychloride are added dropwise while stirring to 4.6 ml. of dimethylformamide. The temperature rises to 30° C. The mixture is treated dropwise with 9.6 g. of 2-butyl-3,5-dimethylanisole, poured onto ice water after the addition of 30 to 35 percent aqueous solution of sodium acetate, stirred for 1 hour and extracted with benzene. The benzene extract is washed with water, dried over sodium sulfate and evaporated. There is obtained 4-methoxy-3-butyl-2,6-dimethyl-benzaldehyde, which is purified by absorption on silica gel, using hexane/methylene chloride 1:1 parts by volume as the eluent, before the condensation with 1-ethoxycarbonyl-2,6-dimethyl-hepta-1,3,5-trien-7-triphenylphosphonium bromide.

Workup

  1. customrises to 30° C
  2. additionThe mixture is treated dropwise with 9.6 g
  3. stirringstirred for 1 hour
  4. extractionextracted with benzene
  5. extractionThe benzene extract
  6. washis washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-89f388d1599a43e69814d9dd9f347813
Source dataset
uspto-grants-1985_07
Patent number
US04532355

Reaction notes

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