Methyl chloroacetate → Trimethyl phosphonoacetate

HRID 1759031Notes

Reaction equation

HRID 1759031 reaction equation
C[O:2][P:3]([O:6][CH3:7])[O:4][CH3:5].Cl[CH2:9][C:10]([O:12][CH3:13])=[O:11]>>[CH3:13][O:12][C:10](=[O:11])[CH2:9][P:3]([O:6][CH3:7])([O:4][CH3:5])=[O:2]

Participants

3

Reactant 2

HCID 7295Methyl chloroacetateHCID 8472Trimethyl phosphite

Product 1

HCID 80029Trimethyl phosphonoacetateYield 75.4%

Procedure

682 g (5.5 M) of trimethylphosphite have been slowly added (21/2 h) to 272 g (2.5 M) of methyl chloroacetate preliminarly heated to 118°. The temperature of the reaction mixture rose at the end of the addition to 125° and was kept at this value for 2 h, whereupon 962 g of raw material was isolated on distillation. A further distillation allowed the obtainment of 344 g (yield 75%) of methyl-dimethylphosphonoacetate having b.p. 125°/8 Torr.

Workup

  1. temperaturepreliminarly heated to 118°
  2. additionThe temperature of the reaction mixture rose at the end of the addition to 125°
  3. customwas isolated on distillation
  4. distillationA further distillation

Sources & evidence

ORD record
ord-753ae4285b7944909babb7d042995966
Source dataset
uspto-grants-1982_07
Patent number
US04338458

Reaction notes

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