Methacrylic Acid → HCID 22140120, compound

HRID 1161618Notes

Reaction equation

HRID 1161618 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C(N(CC)CC)C.[CH2:14]([O:16][CH2:17]Cl)[CH3:15]>ClCCl>[C:1]([O:6][CH2:17][O:16][CH2:14][CH3:15])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 18523Chloromethyl ethyl ether

Product 1

HCID 22140120HCID 22140120, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a 500-mL, 3-necked round bottomed flask equipped with a thermocouple temperature monitor, 250-mL addition funnel, nitrogen inlet and a magnetic stirrer was added 150 mL of dichloromethane, and 18.9 g (0.22 mol) of methacrylic acid. The addition funnel was charged with a mixture of 22.3 g (0.23 mol) of triethylamine and 25 mL of dichloromethane which was then added in a thin stream to the flask with stirring in an ice-bath. Upon completion of the addition, the addition funnel was recharged with a mixture of 18.9 g (0.2 mol) of chloromethyl ethyl ether and 25 mL of dichloromethane which was subsequently added dropwise to the reaction mixture with cooling over about 15 minutes. The ice bath was removed and the mixture stirred at room temperature overnight. The resulting suspension was filtered and the filtrate washed several times with saturated bicarbonate, water and brine and dried over anhydrous magnesium sulfate. Filtration and removal of the solvent by evaporation on a rotary evaporator provided 26.1 g of a yellowish oil which was distilled at reduced pressure to provide 20.3 g (70%) of the title compound as a clear, colorless oil.

Workup

  1. customTo a 500-mL, 3-necked round bottomed flask equipped with a thermocouple temperature monitor, 250-mL addition funnel, nitrogen inlet and a magnetic stirrer
  2. additionwas then added in a thin stream to the flask
  3. additionUpon completion of the addition
  4. additionwas subsequently added dropwise to the reaction mixture
  5. temperaturewith cooling over about 15 minutes
  6. customThe ice bath was removed
  7. stirringthe mixture stirred at room temperature overnight
  8. filtrationThe resulting suspension was filtered
  9. washthe filtrate washed several times with saturated bicarbonate, water and brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationFiltration and removal of the solvent
  12. customby evaporation
  13. customon a rotary evaporator

Sources & evidence

ORD record
ord-37a6981eaf1c4e1195ec08d8421f8560
Source dataset
uspto-grants-2010_10
Patent number
US07820369B2

Reaction notes

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