Triethyl phosphite → Phosphonic acid, (3-methyl-1-oxo-2-butenyl)-, diethyl ester

HRID 1154300Notes

Reaction equation

HRID 1154300 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])[O:2]CC.[CH3:11][C:12]([CH3:17])=[CH:13][C:14](Cl)=[O:15]>C(Cl)Cl>[CH2:9]([O:8][P:1]([C:14](=[O:15])[CH:13]=[C:12]([CH3:17])[CH3:11])(=[O:2])[O:5][CH2:6][CH3:7])[CH3:10]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 11264470Phosphonic acid, (3-methyl-1-oxo-2-butenyl)-, diethyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

83 g (0.5 mol) of triethyl phosphite were added dropwise to a solution of 60 g (0.5 mol) of β,β-dimethylacrylic acid chloride in 200 ml of methylene chloride in the course of one hour. The reaction mixture was stirred for a further hour at 40° to 45° C.; the solvent was then distilled off under reduced pressure and the crude product which remained was purified by vacuum distillation. 90 g (82% of theory) of 1-oxo-3-methyl-2-butene-phosphonic acid diethyl ester of boiling point 72° C./0.01 mbar were obtained.

Workup

  1. distillationthe solvent was then distilled off under reduced pressure
  2. distillationthe crude product which remained was purified by vacuum distillation

Sources & evidence

ORD record
ord-3a1ad008661c4eef8379aadc47867f1a
Source dataset
uspto-grants-1984_12
Patent number
US04489013

Reaction notes

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