1,1-Dichloroethane → HCID 18957260, compound

HRID 903983Notes

Reaction equation

HRID 903983 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7].ClC(Cl)C.[Cl:14][C:15]([Cl:20])([Cl:19])[C:16](Cl)=[O:17]>C(N(CC)CC)C>[Cl:14][C:15]([Cl:20])([Cl:19])[C:16]([O:1][CH2:2][CH2:3][O:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7])=[O:17]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 6420Trichloroacetyl chlorideHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 18957260HCID 18957260, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Hydroxyethylmethacrylate (13.0 g) was placed in a 250 ml, three-necked, round-bottomed flask, fitted with a stirrer, air condenser and two dropping funnels, as well as a thermometer. The apparatus was placed in an ice/salt freezing bath. Dichloroethane (100 ml) was added, followed by the simultaneous dropwise addition of triethylamine (10.1 g) and trichloroacetyl chloride (18.2 g). During the addition the temperature was not allowed to rise above 2° C. After the addition was complete, the mixture was stirred for a further 6 hours, during this time the temperature rose gradually to room temperature. The mixture stood overnight, and the precipitated salt was filtered off, and the residue was washed thoroughly with dichloroethane. The washings and the filtrate were combined and the solvent was removed on a rotary evaporator. The residue still contained some solid. It was dissolved in ether, the ether solution was washed with water (3 times). The solution was then dried (MgSO4), filtered, and the solvent was removed under vacuum. The residue was distilled under high vacuum, collecting the fraction, boiling between 84°-90° C./0.1 mm (16 g).

Workup

  1. customthree-necked, round-bottomed flask, fitted with a stirrer, air condenser
  2. additionDuring the addition the temperature
  3. customto rise above 2° C
  4. additionAfter the addition
  5. customrose gradually to room temperature
  6. waitThe mixture stood overnight
  7. filtrationthe precipitated salt was filtered off
  8. washthe residue was washed thoroughly with dichloroethane
  9. customthe solvent was removed on a rotary evaporator
  10. dissolutionIt was dissolved in ether
  11. washthe ether solution was washed with water (3 times)
  12. dry with materialThe solution was then dried (MgSO4)
  13. filtrationfiltered
  14. customthe solvent was removed under vacuum
  15. distillationThe residue was distilled under high vacuum
  16. customcollecting the fraction
  17. customboiling between 84°-90° C.

Sources & evidence

ORD record
ord-e85cbdeb20f340969142b4237344ed67
Source dataset
uspto-grants-1980_10
Patent number
US04229519

Reaction notes

Loading…