Triethylamine → 4-Allyloxyphenyl methacrylate

HRID 1977003

Reaktionsgleichung

Reaktionsgleichung von HRID 1977003
[C:1]([O:6][C:7](=[O:11])[C:8]([CH3:10])=[CH2:9])(=O)[C:2]([CH3:4])=C.[CH2:12]([O:15][C:16]1C=CC(O)=[CH:18][CH:17]=1)[CH:13]=[CH2:14].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[C:7]([O:6][C:1]1[CH:2]=[CH:4][C:12]([O:15][CH2:16][CH:17]=[CH2:18])=[CH:13][CH:14]=1)(=[O:11])[C:8]([CH3:10])=[CH2:9]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 12974Methacrylic anhydrideHCID 17138834-(Allyloxy)phenol

Produkt 1

HCID 219971104-Allyloxyphenyl methacrylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
37 °C

Versuchsvorschrift

Methacrylic anhydride (6.92 g; 0.045 moles) was added dropwise to a chilled solution of purified 4-allyloxyphenol (7.0 g; 0.047 moles), triethylamine (3.55 g; 0.035 moles), 4-dimethylaminopyridine (0.43 g; 0.004 moles), 2-6-di-tert-butyl-4-methylphenol (0.018 g; 0.08 m moles) and toluene (20 ml) in a stirred 100 ml reaction flask fitted with a reflux condenser, magnetic stirrer and thermocouple probe. During the addition the reaction temperature increased to 37° C. The mixture was heated at 110° C. for 1.5 hour, cooled and washed sequentially with equal volumes of saturated sodium bicarbonate, dilute hydrochloric acid and water. The solution was dried over magnesium sulfate and the solvent removed under reduced pressure to yield 4-allyloxyphenyl methacrylate (8.3 g; 90% yield) as a clear yellow liquid. The structure of the monomer was confirmed by proton and infrared spectral analysis and GC analysis indicated a purity of 90%.

Aufarbeitung

  1. customfitted with a reflux condenser, magnetic stirrer
  2. additionDuring the addition the reaction temperature
  3. temperatureThe mixture was heated at 110° C. for 1.5 hour
  4. temperaturecooled
  5. washwashed sequentially with equal volumes of saturated sodium bicarbonate, dilute hydrochloric acid and water
  6. dry with materialThe solution was dried over magnesium sulfate
  7. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-56186130212a48998657fbb22b253177
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06231714B1

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