Methacrylic Acid → Methacrylic acid, ester with ethyl glycolate

HRID 868289Notes

Reaction equation

HRID 868289 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].Cl[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(N(CC)CC)C>[C:1]([O:6][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 4093Methacrylic AcidHCID 7751Ethyl chloroacetate

Product 1

HCID 30122Methacrylic acid, ester with ethyl glycolate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a flask equipped with a stirrer was added 172.8 parts methacrylic acid and 202 parts triethylamine. This mixture was allowed to stir for 5 min. To this was added 245 parts ethyl chloroacetate. The reactants were heated to 60° C. and the exotherm carried the temperature up to 100° C. The temperature was kept between 90°-97° C. by cooling for 1/2 hour after which heat was supplied to hold the temperature at 90° for 1 hour. The mixture was cooled and filtered. This crude product was distilled at 65.5°-66° C. at 0.1 cm to yield 318 g of pure EMA as confirmed by chemical analysis.

Workup

  1. customTo a flask equipped with a stirrer
  2. customup to 100° C
  3. customwas kept between 90°-97° C.
  4. temperatureby cooling for 1/2 hour after which
  5. temperatureheat
  6. customat 90°
  7. customfor 1 hour
  8. temperatureThe mixture was cooled
  9. filtrationfiltered
  10. distillationThis crude product was distilled at 65.5°-66° C. at 0.1 cm
  11. customto yield 318 g of pure EMA

Sources & evidence

ORD record
ord-886655faae4540108d5165f316d45c22
Source dataset
uspto-grants-1988_10
Patent number
US04778869

Reaction notes

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