Cyclohex-1-en-1-ylphosphonic acid → Cyclohex-1-en-1-ylphosphonic dichloride

HRID 1605537Notes

Reaction equation

HRID 1605537 reaction equation
C1(P(O)(=O)O)CCCCC=1.C(Cl)(Cl)=O.[C:15]1([P:21]([Cl:24])([Cl:23])=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1>>[C:15]1([P:21]([Cl:24])([Cl:23])=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1

Participants

3

Reactant 2

HCID 14979139Cyclohex-1-en-1-ylphosphonic acidHCID 88837489HCID 88837489, compound

Product 1

HCID 23415522Cyclohex-1-en-1-ylphosphonic dichlorideYield 928.2%

Procedure

Into a mixture of 57 g of cyclohexene-1-phosphonic acid and 10 g of cyclohexene-1-phosphonic acid dichloride phosgene was introduced at a temperature of from 170°-180°C for 19 hours. At the end of the reaction, nitrogen was blown through the mixture to remove excess phosgene and subsequently the mixture was distilled under reduced pressure. 62 g of cyclohexene-1-phosphonic acid dichloride were obtained, b.p. 75°C under 0.3 mm Hg, corresponding to a yield of 89.5 percent of the theory.

Workup

  1. additionwas introduced at a temperature of from 170°-180°C for 19 hours
  2. customAt the end of the reaction, nitrogen
  3. customto remove excess phosgene
  4. distillationsubsequently the mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-4d5e81281786499780c91e68c69c95b8
Source dataset
uspto-grants-1976_04
Patent number
US03950413

Reaction notes

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