Phosgene → 3-Cyclohexyloxyacryloyl chloride

HRID 1937058Notes

Reaction equation

HRID 1937058 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH:5]([O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[CH2:6]>>[CH:8]1([O:7][CH:5]=[CH:6][C:1]([Cl:4])=[O:2])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 75129Cyclohexane, (ethenyloxy)-

Product 1

HCID 539683613-Cyclohexyloxyacryloyl chlorideYield 88%

Conditions

Temperature
50 °C

Procedure

50 g (0.5 mol) of phosgene are condensed into a stirred apparatus fitted with −78° C.-cooling. Over a period of 3 hours, 50.5 g (0.4 mol) of cyclohexyl vinyl ether are subsequently added dropwise at 20° C. The mixture is then stirred at 50° C. for 5 hours. The excess phosgene is flushed out with nitrogen, and the crude product is worked up by distillation. At 110° C./2.5 mbar, 66.4 g (88%) of the product of value were obtained.

Workup

  1. customcondensed into a stirred apparatus
  2. customfitted with −78° C.-
  3. temperaturecooling
  4. customThe excess phosgene is flushed out with nitrogen
  5. distillationthe crude product is worked up by distillation

Sources & evidence

ORD record
ord-dffae57b497f45268a46a5de7032e4f8
Source dataset
uspto-grants-2002_05
Patent number
US06392058B1

Reaction notes

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