Acetic Acid → 1,1,4-Triacetoxy-2-methyl-2-butene

HRID 2290940Notes

Reaction equation

HRID 2290940 reaction equation
O=O.[C:3]([O:6][CH:7]=[C:8]([CH3:11])[CH:9]=[CH2:10])(=[O:5])[CH3:4].[C:12]([OH:15])(=[O:14])[CH3:13]>>[C:3]([O:6][CH:7]([O:6][C:3](=[O:5])[CH3:4])[C:8]([CH3:11])=[CH:9][CH2:10][O:14][C:12](=[O:15])[CH3:13])(=[O:5])[CH3:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 977OxygenHCID 544393021-Acetoxy-2-methylbutadiene

Product 1

HCID 538659791,1,4-Triacetoxy-2-methyl-2-buteneYield 58.8%

Procedure

12,000 parts by volume of oxygen are introduced in the course of 4 hours into a solution, at 95° C., of 63 parts of 1-acetoxy-2-methyl-1,3-butadiene in 600 parts of glacial acetic acid, in which 25 parts of the catalyst prepared as described in Example 1a are suspended. The reaction mixture is worked up as described in Example 1b and fractional distillation gives 71.8 parts of 1,1,4-triacetoxy-2-methyl-2-butene (representing 58.8% conversion) of boiling point 118°-124° C./0.7 mbar and 19.5 parts of 4-acetoxytiglic aldehyde (representing 27.4% conversion) of boiling point 102°-107° C./25-27 mbar.

Workup

  1. customprepared
  2. distillationas described in Example 1b and fractional distillation

Sources & evidence

ORD record
ord-c7413cd7828146eca3fdd097a3627be2
Source dataset
uspto-grants-1986_10
Patent number
US04618704

Reaction notes

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