Triphenylphosphine → Phosphonic dichloride, (2-methylphenyl)-

HRID 1249607Notes

Reaction equation

HRID 1249607 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[P:7]([Cl:10])([Cl:9])=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[Cl:9][P:7]([Cl:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:11].[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[P:7]([Cl:9])([Cl:10])=[O:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 10921725Phosphonic dichloride, (2-methylphenyl)-

Product 2

HCID 10921725Phosphonic dichloride, (2-methylphenyl)-HCID 14226801Phosphonous dichloride, (2-methylphenyl)-

Procedure

317 g (1.52 moles) of o-tolylphosphonic acid dichloride and 400 g (1.53 moles) of triphenylphosphane were stirred for 17 hours at 180° C. under an atmosphere of nitrogen. The mixture was then cooled and the triphenylphosphane oxide which had crystallized out was filtered off with suction. The filtrate was distilled at 0.093 kPa at a top temperature of approx. 80°-100° C. This gave 220 g, containing 45% of dichloro-o-tolylphosphane and 45% of o-tolylphosphonic acid dichloride (according to 31P-NMR spectrum). The dichloro-o-tolylphosphane was obtained at a yield of 50% of theory, at a 68.5% conversion of o-tolylphosphonic acid dichloride.

Workup

  1. temperatureThe mixture was then cooled
  2. customthe triphenylphosphane oxide which had crystallized out
  3. filtrationwas filtered off with suction
  4. distillationThe filtrate was distilled at 0.093 kPa at a top temperature of approx. 80°-100° C
  5. additionThis gave 220 g, containing 45% of dichloro-o-tolylphosphane and 45% of o-tolylphosphonic acid dichloride (according to 31P-NMR spectrum)

Sources & evidence

ORD record
ord-e7590209ead8497b82555773e233545d
Source dataset
uspto-grants-1986_12
Patent number
US04632995

Reaction notes

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