Phosphorus oxychloride → 4-Allyloxy-2,6-dimethyl-benzaldehyde

HRID 1369938Notes

Reaction equation

HRID 1369938 reaction equation
CN([CH:9]=[O:10])C1C=CC=CC=1.P(Cl)(Cl)(Cl)=O.[CH3:16][C:17]1[CH:18]=[C:19]([O:24][CH2:25][CH:26]=[CH2:27])[CH:20]=[C:21]([CH3:23])[CH:22]=1>>[CH2:25]([O:24][C:19]1[CH:20]=[C:21]([CH3:23])[C:22]([CH:9]=[O:10])=[C:17]([CH3:16])[CH:18]=1)[CH:26]=[CH2:27]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 257959Allyl 3,5-dimethylphenyl ether

Product 1

HCID 185158104-Allyloxy-2,6-dimethyl-benzaldehydeYield 51%

Conditions

Temperature
70 °C

Procedure

N-methyl formanilide, 20.5 ml (166 mmole), was chilled to 13°, where it began to solidify. Phosphorus oxychloride, 14.4 ml (155 mmole), was added with stirring, under nitrogen. After 25 minutes, the temperature was 45°. 3,5-Dimethylallyloxy benzene, 16.2 g (100 mmole), prepared as describe above, was added with stirring and heated in a 70° C. oil bath. The reaction exothermed to 93° C. and was stirred under nitrogen for 30 minutes. The bath was removed and when the temperature reached 35°, the product was dissolved in chloroform. Ice was added, the layers were separated and washed once with water, twice with sodium bicarbonate, once with water and once with brine. The product was chromatographed down 500 ml of silica, eluting with chloroform to give 9.67 g (51%) of subtitled product which was used without further purification.

Workup

  1. customwas 45°
  2. additionwas added
  3. stirringwith stirring
  4. customexothermed to 93° C.
  5. stirringwas stirred under nitrogen for 30 minutes
  6. customThe bath was removed
  7. customreached 35°
  8. dissolutionthe product was dissolved in chloroform
  9. additionIce was added
  10. customthe layers were separated
  11. washwashed once with water, twice with sodium bicarbonate, once with water and once with brine
  12. customThe product was chromatographed down 500 ml of silica
  13. washeluting with chloroform

Sources & evidence

ORD record
ord-9250ddbc7f6a47f7a68532bb0df6b29c
Source dataset
uspto-grants-2003_06
Patent number
US06579871B2

Reaction notes

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