Acetyl chloride → DIMETHYL ACETYLPHOSPHONATE

HRID 1109641Notes

Reaction equation

HRID 1109641 reaction equation
[P:1]([O:6][CH3:7])([O:4][CH3:5])[O:2]C.[C:8](Cl)(=[O:10])[CH3:9]>>[C:8]([P:1](=[O:2])([O:6][CH3:7])[O:4][CH3:5])(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 8472Trimethyl phosphite

Product 1

HCID 2785315DIMETHYL ACETYLPHOSPHONATEYield 44%

Procedure

Trimethyl phosphite (57.1 g, 0.46 mol) is added dropwise to an ice cold solution of acetyl chloride (36.2, 0.26 nol) at a rate that the internal temperature did not rise above 5° C. The ice bath is removed and the solution warmed to room temperature and then heated to 100° C. for 1 hour. The solution is then vacuum distilled through a 12-inch Vigeraux column to give 30.87 g, 44% of a clear liquid with bp 57°-60° C. at 0.5 mm. H and C nmr are consistent with the assigned structure. This procedure is adapted from the published method of McConnell, R. L., Coover, H. W.,Jr. J. Am. Chem. Soc., 1956, 78, 4450-4452. ##STR20##

Workup

  1. customdid not rise above 5° C
  2. customThe ice bath is removed
  3. temperatureheated to 100° C. for 1 hour
  4. distillationvacuum distilled through a 12-inch Vigeraux column

Sources & evidence

ORD record
ord-a541d43f25114d1faae78907e5486518
Source dataset
uspto-grants-1994_06
Patent number
US05321153

Reaction notes

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