Phosphorus pentachloride → HCID 86586929, compound

HRID 1356935Notes

Reaction equation

HRID 1356935 reaction equation
[CH2:1]([CH:3]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:4][O:5][C:6](=[O:12])/[CH:7]=[CH:8]\[C:9]([O-:11])=[O:10])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:18]>>[Cl-:18].[CH2:1]([CH:3]([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:4][O:5][C:6](=[O:12])/[CH:7]=[CH:8]\[C:9]([OH:11])=[O:10])[CH3:2]

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 86586930HCID 86586930, compound

Product 1

HCID 86586929HCID 86586929, compoundYield 92%

Conditions

Temperature
60 °C

Procedure

A 4.1 g (20 mmol) quantity of mono(2-ethylhexyl)maleate manufactured by Aldrich Co. was slowly added dropwise to 4.1 g (20 mmol) of phosphorus pentachloride while maintaining a temperature not greater than 30° C. When the dropwise addition had been completed, stirring was conducted for 1 hr at room temperature. Subsequently, the mixture was heated to 60° C., the pressure was reduced with an aspirator, and the phosphorus oxychloride was distilled off, yielding 4.5 g (yield of 92 percent) of maleic acid mono(2-ethylhexyl)ester monochloride in the form of a tea-colored oily product.

Workup

  1. temperaturewhile maintaining a temperature not greater than 30° C
  2. additionWhen the dropwise addition
  3. distillationthe phosphorus oxychloride was distilled off

Sources & evidence

ORD record
ord-404945633c484bae83aadf8156eabba9
Source dataset
uspto-grants-2003_07
Patent number
US06589723B2

Reaction notes

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