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

HRID 275229

Reaction equation

HRID 275229 reaction equation
[P:1]([Cl:5])(Cl)(Cl)=[S:2].C(N([CH2:11][CH3:12])CC)C.[CH3:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:15]=1[OH:21]>C1(C)C=CC=CC=1>[P:1]([Cl:5])([O:21][C:15]1[CH:14]=[CH:19][C:18]([CH3:20])=[CH:17][C:11]=1[CH3:12])([O:21][C:15]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:14]=1[CH3:13])=[S:2]

Participants

5

Reactant 3

HCID 77712,4-DimethylphenolHCID 8471TriethylamineHCID 19883Thiophosphoryl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

Thiophosphoryl chloride (17.0 g) was dissolved in toluene (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 triethylamine 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 H3PO4).

Workup

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

Sources & evidence

ORD record
ord-a9566929acc14ba1b7e6acdc2647a06b
Source dataset
uspto-grants-1995_02
Patent number
US05393431

Linked notes

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