Propionic Acid → 3,3-Bis(vinyloxymethyl)oxetane

HRID 872424

Reaktionsgleichung

Reaktionsgleichung von HRID 872424
C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)[CH2:8][CH3:9].[C:12](OC=C)(=O)[CH3:13].[O:18]1[CH2:21][C:20]([CH2:24][OH:25])([CH2:22][OH:23])[CH2:19]1>C1(C)C=CC=CC=1>[CH:12]([O:23][CH2:22][C:20]1([CH2:24][O:25][CH:8]=[CH2:9])[CH2:21][O:18][CH2:19]1)=[CH2:13]

Komponenten

6

Edukt 4

HCID 1032Propionic AcidHCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 5292293,3-Bis(hydroxymethyl)oxetane

Produkt 1

HCID 251582843,3-Bis(vinyloxymethyl)oxetaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture (280 ml) of 24.9 g (0.23 mol) of sodium carbonate with toluene was raised in temperature to 95° C., 1.4 g of propionic acid was added, and, while maintaining the temperature at 95° C., 16 g of vinyl acetate was added dropwise, and 15 minutes later, 1.27 g (1.9 mmol) of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 was further added. Next, 40 g (0.19 mol) of oxetane-3,3-dimethanol was added dropwise over 3 hours for a reaction. After the completion of the dropwise addition and subsequent stirring for 1 hour, the reaction mixture was analyzed by gas chromatography and found that there were formed 3,3-bis(vinyloxymethyl)oxetane represented by the following formula in a yield of 90% and (3-vinyloxymethyloxetan-3-yl)methanol in a yield of 2%. The reaction mixture was purified by distillation and thereby yielded 31 g of 3,3-bis(vinyloxymethyl)oxetane with a purity of 99%.

Aufarbeitung

  1. additionAfter the completion of the dropwise addition

Quellen und Nachweise

ORD-Eintrag
ord-7fe1e2759a4f451cadff055525ab1027
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975349B2

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