Pyridine → HCID 21421268, compound

HRID 435583Notes

Reaction equation

HRID 435583 reaction equation
N1C=CC=CC=1.[C:7]([O:12][CH2:13][CH2:14][O:15][CH:16](O)[C:17]([Cl:20])([Cl:19])[Cl:18])(=[O:11])[C:8]([CH3:10])=[CH2:9].O=CC(Cl)(Cl)[Cl:25].CC(C(OCCO)=O)=C>C(OCC)C.S(Cl)(Cl)=O>[C:7]([O:12][CH2:13][CH2:14][O:15][CH:16]([Cl:25])[C:17]([Cl:20])([Cl:19])[Cl:18])(=[O:11])[C:8]([CH3:10])=[CH2:9]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6407ChloralHCID 133602-Hydroxyethyl MethacrylateHCID 21421270HCID 21421270, compound

Product 1

HCID 21421268HCID 21421268, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
20 °C

Procedure

Pyridine (75 ml) in 500 ml of diethyl ether and 65 ml of thionyl chloride are mixed while being stirred and cooled by an ice-water bath in a flask provided with a mechanical stirrer, a reflux condenser and a dropping funnel. A solution of 220 g of crystalline 2-(1-hydroxy-2,2,2-trichloroethoxy)ethyl methacrylate (m.p. 44-45° C; prepared by the addition of chloral to glycol monomethacrylate) in 500 ml of diethyl ether is slowly added to the mixture during continuous stirring and cooling. After all of the hydroxy compound has been added into the reactor, the reaction mixture is stirred and cooled for further 2 hours. It is then warmed to the temperature 20° C, the precipitated pyridine hydrochloride is filtered off and ether is removed by distillation. The distillation residue is heated in the presence of 20 g of powdered copper to the temperature 80° C at the pressure 15 Torr for 2 hrs and then it is rectified through an effective column. By a repeated fraction distillation, 180 g of 2-(1,2,2,2-tetrachloroethoxy)ethyl methacrylate was obtained, having b.p. 96 - 97° C 0.1 Torr and refractive index nD25 1.4900. Elemental analysis: found C 32.20%, H 3.58%, Cl 47.35%; calculated C 32.46%, H 3.40%, Cl 47.90%.

Workup

  1. temperaturecooled by an ice-water bath in a flask
  2. customprovided with a mechanical stirrer, a reflux condenser and a dropping funnel
  3. additionis slowly added to the mixture
  4. stirringduring continuous stirring
  5. temperaturecooling
  6. stirringthe reaction mixture is stirred
  7. temperaturecooled for further 2 hours
  8. filtrationthe precipitated pyridine hydrochloride is filtered off
  9. customether is removed by distillation
  10. temperatureThe distillation residue is heated in the presence of 20 g of powdered copper to the temperature 80° C at the pressure 15 Torr for 2 hrs
  11. distillationBy a repeated fraction distillation

Sources & evidence

ORD record
ord-b4719d7fcffd48a8b9c8c0da6e697445
Source dataset
uspto-grants-1977_02
Patent number
US04006147

Reaction notes

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