3-Chloro-2-chloromethyl-1-propene → HCID 54311690, compound

HRID 1580917Notes

Reaction equation

HRID 1580917 reaction equation
[CH2:1]=[C:2]([CH2:5]Cl)[CH2:3][Cl:4].[P:7]([O:14]CC)([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10]>>[CH2:9]([O:8][P:7]([CH2:5][C:2](=[CH2:1])[CH2:3][Cl:4])(=[O:14])[O:11][CH2:12][CH3:13])[CH3:10]

Participants

3

Reactant 2

HCID 158593-Chloro-2-chloromethyl-1-propeneHCID 31215Triethyl phosphite

Product 1

HCID 54311690HCID 54311690, compound

Conditions

Temperature
180 °C

Procedure

34 parts by weight of 2-methylene propane-1,3-dichloride are heated to 135°C, after which 30 parts by weight of triethyl phosphite are added dropwise with stirring, Ethyl chloride distills off continuously during the dropwise addition. On completion of the dropwise addition, the reaction temperature is increased slowly to 180°C. After 3 to 4 hours at 180°C, the evolution of ethyl chloride is at an end and the reaction is over. The excess dihalide is distilled off in a water-jet vacuum. The resulting 1-chloro-2-methylene propane-3-phosphonic acid diethyl ester is distilled off in a high vacuum.

Workup

  1. distillationEthyl chloride distills off continuously during the dropwise addition
  2. additionOn completion of the dropwise addition
  3. distillationThe excess dihalide is distilled off in a water-jet vacuum
  4. distillationThe resulting 1-chloro-2-methylene propane-3-phosphonic acid diethyl ester is distilled off in a high vacuum

Sources & evidence

ORD record
ord-486f671d87fd4f2ba835ff00f00d4440
Source dataset
uspto-grants-1976_01
Patent number
US03935174

Reaction notes

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