Toluene → 2-Propenoic acid, 2-methyl-, 2-(2-propen-1-yloxy)ethyl ester

HRID 433342

Reaktionsgleichung

Reaktionsgleichung von HRID 433342
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([O:10][CH2:11][CH2:12]O)[CH:8]=[CH2:9].C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:1]([O:6][CH2:12][CH2:11][O:10][CH2:7][CH:8]=[CH2:9])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Komponenten

6

Edukt 3

HCID 1140TolueneHCID 4093Methacrylic AcidHCID 8116Ethylene glycol monoallyl ether

Produkt 1

HCID 856092-Propenoic acid, 2-methyl-, 2-(2-propen-1-yloxy)ethyl esterAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysator3×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a three-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a Dean-Stark apparatus were added methacrylic acid (137.7 g, 1.6 moles), ethyleneglycol monoallylether (80.7 g, 0.8 moles), p-toluenesulfonic acid (0.76 g, 4.0 mmole) and toluene (650 mL). The mixture was heated to 120° C. for 5 hours with exclusion of water. Another portion of p-toluenesulfonic acid (0.12 g) and the mixture was heated to 120° C. for 6 hours. The other portion of p-toluenesulfonic acid (0.1 g) was added and the mixture was heated to 120° C. for 9 hours. During the reaction, the consumption of methacrylic acid and ethyleneglycol monoallylether were monitored by liquid chromatography and the conversion reached 98%. The mixture was neutralized by addition of aq. NaHCO3 and the layers were separated. The aqueous layer was extracted with toluene and the combined organic layers were dried over CaCl2 and concentrated under reduced pressure. Distillation of the crude material (60° C. at 2 mmng) yielded 2-allyloxyethyl methacrylate (98.7 g, 73%) shown below.

Aufarbeitung

  1. customTo a three-necked flask equipped with a stirrer
  2. customDuring the reaction
  3. customthe consumption of methacrylic acid and ethyleneglycol monoallylether
  4. additionThe mixture was neutralized by addition of aq. NaHCO3
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with toluene
  7. dry with materialthe combined organic layers were dried over CaCl2
  8. concentrationconcentrated under reduced pressure
  9. distillationDistillation of the crude material (60° C. at 2 mmng)

Quellen und Nachweise

ORD-Eintrag
ord-6282a7564d944b00afc83c3a63874e64
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667369B2

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