Reaktion #89620

ord-eba05cae420d4eb5ae930194eb321a31

Reaktionsgleichung

C=CC(=C)C
Isoprene
COC(=O)/C=C\C(=O)OC
dimethyl maleate
COC(=O)C1CC=C(C)CC1C(=O)OC
4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester
Ausbeute 66.7%

Reaktionsbedingungen

Temperatur
150°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe autoclave was sealed
  2. 2
    TemperaturThe temperature of the autoclave increased to 195° C. due to the
  3. 3
    Temperaturheat of the reaction
  4. 4
    Sonstigethe completion of the reaction
  5. 5
    TemperaturThe autoclave was then cooled to room temperature
  6. 6
    workup.DISTILLATIONSimple distillation of the resulting mixture

Vorschrift

Isoprene (350 g, 5.1 mol) and dimethyl maleate (741 g, 5.1 mol) were loaded into a stainless steel autoclave. The autoclave was sealed and heated to 150° C. The temperature of the autoclave increased to 195° C. due to the heat of the reaction. The temperature was held at 160° C. for 1 hour. Gas chromatography (GC) analysis indicated the completion of the reaction. The autoclave was then cooled to room temperature. Simple distillation of the resulting mixture provided 4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester (725 g, 3.4 mol, 66% yield) as a light yellow liquid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09441185B2uspto-grants-2016_09