Methacrylic Acid → 1-Ethoxyethyl Methacrylate (stabilized with MEHQ)

HRID 1741225Notes

Reaction equation

HRID 1741225 reaction equation
C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[CH:15]([O:17][CH2:18][CH3:19])=[CH2:16].[C:20]([OH:25])(=[O:24])[C:21]([CH3:23])=[CH2:22].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>S([O-])([O-])(=O)=O.[Na+].[Na+]>[C:20]([O:25][CH:15]([O:17][CH2:18][CH3:19])[CH3:16])(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

7

Reactant 5

HCID 4093Methacrylic AcidHCID 7108PhenothiazineHCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 201933451-Ethoxyethyl Methacrylate (stabilized with MEHQ)Yield 84.7%

Reagents, catalysts & solvents 1

HCID 24436Sodium SulfateCatalyst

Procedure

0.5 Grams of phenothiazin is added to 144.2 g (2 moles) of ethyl vinyl ether and 86.1 g (1 mole) of methacrylic acid is dropwise added thereto at 10° C. or lower, followed by stirring at room temperature for 4 hours. 5.0 Grams of pyridinium p-toluenesulfonate is added to the resultant, followed by conducting a reaction with stirring at room temperature for 2 hours and allowing to stand for overnight at room temperature. 5 Grams of sodium bicarbonate and 5 g of sodium sulfate are added to the reaction solution, followed by stirring at room temperature for 1 hour. Insolubles are removed by filtration and concentration under reduced pressure is conducted, and the yellow oily residue is distilled under reduced pressure to give 134.0 g of 1-ethoxyethyl methacrylate as colorless oily fraction having bp. 43 to 45° C./7mmHg.

Workup

  1. additionis dropwise added
  2. customat 10° C.
  3. customa reaction
  4. stirringwith stirring at room temperature for 2 hours
  5. waitto stand for overnight at room temperature
  6. stirringby stirring at room temperature for 1 hour
  7. customInsolubles are removed by filtration and concentration under reduced pressure
  8. distillationthe yellow oily residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-ecb12f1ae3fc4aca81116bc3ae1015f6
Source dataset
uspto-grants-1999_10
Patent number
US05973094

Reaction notes

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