Methyl Chloride → Dimethyl allylphosphonate

HRID 328545Notes

Reaction equation

HRID 328545 reaction equation
[P:1]([O:6]C)([O:4][CH3:5])[O:2][CH3:3].[CH2:8](Cl)[CH:9]=[CH2:10].CCl>[Ni]>[CH3:3][O:2][P:1]([CH2:10][CH:9]=[CH2:8])(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 6327Methyl ChlorideHCID 7850Allyl chlorideHCID 8472Trimethyl phosphite

Product 1

HCID 136570Dimethyl allylphosphonate

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

124 parts of trimethyl phosphite, together with 1 part of Raney nickel, are heated for 1 hour to 130°-140° C in a nitrogen atmosphere. 80 parts of allyl chloride are then slowly added dropwise so that the temperature does not fall below 80° to 90° C. The methyl chloride formed escapes through the reflux condenser. The reaction is over after 22 hours. The Raney nickel is filtered off, followed by fractionation in vacuo. Bp: 83°-84° C/12 Torr; nD20 : 1.4371; Yield: 86 parts, corresponding to 57% of the theoretical.

Workup

  1. customdoes not fall below 80° to 90° C
  2. customafter 22 hours
  3. filtrationThe Raney nickel is filtered off

Sources & evidence

ORD record
ord-3735518422f9471fb81ad38dd9e52280
Source dataset
uspto-grants-1977_04
Patent number
US04017564

Reaction notes

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