Isoprene → 4-Cyclohexene-1,2-dicarboxylic acid, 4-methyl-, dimethyl ester

HRID 61342

Reaction equation

HRID 61342 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[C:6]([O:14][CH3:15])(=[O:13])/[CH:7]=[CH:8]\[C:9]([O:11][CH3:12])=[O:10]>>[CH3:12][O:11][C:9]([CH:8]1[CH2:1][CH:2]=[C:3]([CH3:5])[CH2:4][CH:7]1[C:6]([O:14][CH3:15])=[O:13])=[O:10]

Participants

3

Reactant 2

HCID 6557IsopreneHCID 5271565Dimethyl maleate

Product 1

HCID 2743794-Cyclohexene-1,2-dicarboxylic acid, 4-methyl-, dimethyl esterYield 66.7%

Conditions

Temperature
150 °C

Procedure

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.

Workup

  1. customThe autoclave was sealed
  2. temperatureThe temperature of the autoclave increased to 195° C. due to the
  3. temperatureheat of the reaction
  4. customthe completion of the reaction
  5. temperatureThe autoclave was then cooled to room temperature
  6. distillationSimple distillation of the resulting mixture

Sources & evidence

ORD record
ord-eba05cae420d4eb5ae930194eb321a31
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Linked notes

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