Ethylene → 1,1,3-Trichloropropane-1-phosphonic dichloride

HRID 1438898Notes

Reaction equation

HRID 1438898 reaction equation
[CH2:1]=C.[Cl:3][C:4]([Cl:10])(Cl)[P:5]([Cl:8])([Cl:7])=[O:6].[CH2:11]([Cl:13])Cl>[Ag]>[Cl:3][C:4]([Cl:10])([P:5]([Cl:8])([Cl:7])=[O:6])[CH2:1][CH2:11][Cl:13]

Participants

5

Reactant 3

HCID 6325EthyleneHCID 6344DichloromethaneHCID 277422(Trichloromethyl)phosphonic dichloride

Product 1

HCID 213996851,1,3-Trichloropropane-1-phosphonic dichloride

Reagents, catalysts & solvents 1

HCID 23954SilverCatalyst

Procedure

5.6 g (0.2 mole) ethylene, 23.6 g (0.1 mole) trichloromethane phosphonic dichloride, 162 mg (1 mmole) anhydrous ferric chloride and 366 mg (1 mmole) dibenzpinacol were heated in a 100 ml silver-lined autoclave in 40 ml dry methylene chloride at 120° during 14 hours. During this time the pressure fell from 500 to 220 psi. After cooling, the reaction product was extracted three times with ice-cold 1N aqueous hydrochloric acid after take-up in methylene chloride and dried on calcium chloride. Evaporation at atmospheric pressure at 50° left an oil which was distilled in vacuo, yielding 13.7 g 1,1,3-trichloropropane-1-phosphonic dichloride, bp/4: 105° -106°. Quantitative half-hydrolysis gave 13.4% chloride ion. Calc.: 13.4%.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction product was extracted three times with ice-cold 1N aqueous hydrochloric acid
  3. customdried on calcium chloride
  4. customEvaporation at atmospheric pressure at 50°
  5. waitleft an oil which
  6. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-6199cee6f50946348541aead0a6b5377
Source dataset
uspto-grants-1977_11
Patent number
US04057578

Reaction notes

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