Acetic Acid → 3,4-Diacetoxy-1-butene

HRID 54724

Reaction equation

[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(CCCC)CCCC)CCC.[C:26](O)(=[O:28])[CH3:27]>COCCOCCOC>[C:6]([O:9][CH:2]([CH2:5][O:1][C:26](=[O:28])[CH3:27])[CH:3]=[CH2:4])(=[O:8])[CH3:7]

Participants

Conditions

Temperature: 125 °C

Procedure

A 300-mL autoclave was charged with 40 mL (0.50 mol) of 3,4-epoxy-1-butene, 60.0 g (0.59 mol) acetic anhydride, 3.7 g (0.02 mol) of tributylamine, 0.72 g (0.012 mol) acetic acid 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 hrs, samples were taken every 15 min for analysis by GC. GC analysis of the crude mixture after 2 hrs revealed a 79% yield of 3,4-diacetoxy-1-butene with a 90% selectivity and 12% 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 0.017 min-1 (Table A). This example shows the catalytic effect of another tertiary amine with acetic acid as the co-catalyst.

Workup

customThe autoclave was purged with nitrogen twice
waitGC analysis of the crude mixture after 2 hrs revealed

Sources & evidence

ORD record: ord-3aa2160cfd7d48bfb175aee0e666131a
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05623086

Linked notes

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