Chloroethane → Diethyl acetylphosphonate

HRID 325260

Reaction equation

HRID 325260 reaction equation
[P:1]([O:9][CH2:10][CH3:11])([O:6][CH2:7][CH3:8])([O:3]CC)=O.[C:12](Cl)(=[O:14])[CH3:13].C(Cl)C>>[C:12]([P:1](=[O:3])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11])(=[O:14])[CH3:13]

Participants

4

Reactant 3

HCID 6337Chloroethane2×HCID 6367Acetyl chlorideHCID 6535Triethyl Phosphate

Product 1

HCID 522997Diethyl acetylphosphonateYield 98%

Procedure

166.2 grams (1 mole) triethyl phosphate was added dropwise with stirring to 78.4 grams (1 mole) of acetyl chloride over a period of 30 minutes at a temperature of 30° to 35° C. maintained by cooling. Ethyl chloride was evolved. The temperature was increased to 60° C. over the next 1 hour and 15 minutes, at which time the evolution of ethyl chloride was complete. The product was distilled under vaccum yielding 176 grams of diethyl acetylphosphonate (DEAP) in 98% yield, B.P. about 80° C. at 5 mm. and having a refractive index of 1.4240 at 200° C.

Workup

  1. temperaturemaintained
  2. temperatureby cooling
  3. distillationThe product was distilled under vaccum

Sources & evidence

ORD record
ord-e23e4fc29f8149ea9d146b841f182704
Source dataset
uspto-grants-1984_04
Patent number
US04440646

Linked notes

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