Ethanol → HCID 86736268, compound

HRID 2163830Notes

Reaction equation

HRID 2163830 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].C([OH:7])C.[C:8]([O:13][CH2:14][CH2:15]O)(=[O:12])[C:9]([CH3:11])=[CH2:10].N1C=CC=CC=1>C(Cl)Cl>[Cl:4][C:1]([OH:2])=[O:7].[C:8]([O:13][CH2:14][CH3:15])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 6371PhosgeneHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 86736268HCID 86736268, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

750 g (6 mols + 25%) of phosgene and 2 liters of dry, ethanol-free methylene chloride were placed in a 10 liter reactor, cooled to -30° C. A solution of 6 mols (780 g) of hydroxyethyl methacrylate and 6 mols (480 g) of pyridine in 1 liter of methylene chloride was added to this mixture over a period of 1 hour 30 minutes, the temperature being kept at between -10° and -15° C. After two hours of stirring at -10° C., the excess phosgene was removed by degassing with nitrogen. After removing the pyridine hydrochloride by filtration, the solution was rapidly washed with 2 liters of ice-cold water. The organic phase was decanted, dried over magnesium sulphate and concentrated under reduced pressure; 1,040 g of ethyl methacrylate chloroformate were thus obtained in a yield of 90%.

Workup

  1. custombeing kept at between -10° and -15° C
  2. customthe excess phosgene was removed
  3. customby degassing with nitrogen
  4. customAfter removing the pyridine hydrochloride
  5. filtrationby filtration
  6. washthe solution was rapidly washed with 2 liters of ice-cold water
  7. customThe organic phase was decanted
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a99149fe1f1a4a6da1dae15a23b6b76d
Source dataset
uspto-grants-1979_01
Patent number
US04137253

Reaction notes

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