Acetic Anhydride → 3,4-Diacetoxy-1-butene

HRID 54722

Reaktionsgleichung

[O:1]1[CH2:5][CH:2]1[CH:3]=[CH2:4].[C:6]([O:9]C(=O)C)(=[O:8])[CH3:7].C(N(CC)CC)C.C[O:21][CH2:22][CH2:23]OCCOC>>[C:6]([O:9][CH:2]([CH2:5][O:1][C:22](=[O:21])[CH3:23])[CH:3]=[CH2:4])(=[O:8])[CH3:7]

Komponenten

Edukt 4

HCID 7918Acetic Anhydride

HCID 8150Diglyme

HCID 8471Triethylamine

HCID 13586Vinyloxirane

Produkt 1

HCID 27350013,4-Diacetoxy-1-buteneAusbeute 92 %

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

A 300-mL autoclave was charged with 40 mL (0.50 mol) of 3,4-epoxy-1-butene, 63.2 g (0.62 mol) acetic anhydride, 4.06 g (0.041 mol) of triethylamine and 4.2 mL of diglyme. The autoclave was purged with nitrogen twice, then the vessel was pressurized to 8 bars (100 psig) with nitrogen. The agitator was started and an initial sample was taken. The mixture was heated to 125° C. During the course of 2.5 hrs, samples were taken every 15 min for analysis by GC. GC analysis of the crude mixture after 2.5 hrs revealed a 92% yield of 3,4-diacetoxy-1-butene with a 92% selectivity and 0.36% 3,4-epoxy-1-butene. The reaction was observed to be first order in 3,4-epoxy-1-butene with a first order rate constant of 0.037 min-1 (Table A). This example demonstrates the catalytic effect of the tertiary amine alone.

Aufarbeitung

customThe autoclave was purged with nitrogen twice
waitGC analysis of the crude mixture after 2.5 hrs revealed

Quellen und Nachweise

ORD-Eintrag: ord-6e6ef29129cb420f913406ea274eb835
Quelldatensatz: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05623086

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