O-Xylene → HCID 11041943, compound

HRID 1732564Notes

Reaction equation

HRID 1732564 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[P:5]([Cl:8])(Cl)[Cl:6].[CH3:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[CH3:16]>>[CH3:9][C:10]1[CH:11]=[C:12]([P:5]([Cl:8])[Cl:6])[CH:13]=[CH:14][C:15]=1[CH3:16]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 24387Phosphorus trichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11041943HCID 11041943, compoundYield 65.6%

Procedure

A mixture of carefully dried o-xylene (29.9 g), freshly prepared anhydrous aluminium trichloride (56 g) and freshly distilled phosphorus trichloride (172.6 g) was refluxed gently, with stirring, for 2 hours. The mixture was then refluxed vigorously for a further 11/2 hours. The source of heat was removed and freshly distilled phosphoryl chloride (64.5 g) added to the mixture dropwise, with stirring, so that reflux was maintained; a white solid precipitated during the addition. The reaction mixture was allowed to cool to room temperature and dry pentane (100 ml) was added and the resultant mixture stirred for several hours, after which the precipitated solids were filtered off and washed with dry pentane. Volatile products were removed from the combined filtrates under reduced pressure, and the resulting yellow oil was fractionally distilled under reduced pressure. The required product 3,4-dimethylphenyl phosphonous dichloride (58 g) was distilled at a pressure of 0.05 mmHg at 78°-80° C. This was equivalent to a yield of 65.6% based on o-xylene. It was a colourless liquid.

Workup

  1. temperaturewas refluxed gently
  2. temperatureThe mixture was then refluxed vigorously for a further 11/2 hours
  3. temperatureThe source of heat
  4. customwas removed
  5. additionfreshly distilled phosphoryl chloride (64.5 g) added to the mixture dropwise
  6. stirringwith stirring
  7. temperatureso that reflux
  8. temperaturewas maintained
  9. customa white solid precipitated during the addition
  10. additiondry pentane (100 ml) was added
  11. stirringthe resultant mixture stirred for several hours
  12. filtrationafter which the precipitated solids were filtered off
  13. washwashed with dry pentane
  14. customVolatile products were removed from the combined filtrates under reduced pressure
  15. distillationthe resulting yellow oil was fractionally distilled under reduced pressure
  16. distillationThe required product 3,4-dimethylphenyl phosphonous dichloride (58 g) was distilled at a pressure of 0.05 mmHg at 78°-80° C

Sources & evidence

ORD record
ord-1b031c5c6d0e426e97643eeff26292f1
Source dataset
uspto-grants-1980_12
Patent number
US04238422

Reaction notes

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