2,4-Dimethylphenol → Bis(2,4-dimethylphenyl) chlorothiophosphate

HRID 2362

Reaction equation

HRID 2362 reaction equation
[P:1]([Cl:5])(Cl)(Cl)=[S:2].[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[OH:14]>C(N(CC)CC)C>[P:1]([Cl:5])([O:14][C:8]1[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=1[CH3:6])([O:14][C:8]1[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=1[CH3:6])=[S:2]

Participants

4

Reactant 2

HCID 77712,4-DimethylphenolHCID 19883Thiophosphoryl chloride

Product 1

HCID 19690204Bis(2,4-dimethylphenyl) chlorothiophosphateYield 89.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

Thiophosphoryl chloride (17.0 g) was dissolved in tuoluene (250 cm3) and triethylamine (21.5 g) was added. The solution was stirred at 20° C. and 2,4-dimethylphenol (24.4 g) was added in portions during 1 hr. The mixture was stirred for 2 hr. and then heated and stirred at 80° C. for a further 2 hr. and then cooled and filtered to remove thriethylamine hydrochloride. The toluene was distilled under reduced pressure leaving bis(2,4-dimethylphenyl) chlorothiophosphate (oil, 30.6 g. 31P NMR in CDCl3, singlet 54.57 ppm downfield of H3 PO4).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 2 hr
  3. temperatureand then heated
  4. stirringstirred at 80° C. for a further 2 hr
  5. temperatureand then cooled
  6. filtrationfiltered
  7. customto remove thriethylamine hydrochloride
  8. distillationThe toluene was distilled under reduced pressure

Sources & evidence

ORD record
ord-0308ebab0a1b4896a483600b07def253
Source dataset
uspto-grants-1998_03
Patent number
US05728853

Linked notes

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