1,3-Butadiene → 1-Phenyl-4-cyclohexene-1,2-dicarboxylic acid anhydride

HRID 441839

Reaction equation

HRID 441839 reaction equation
[C:1]1([C:7]2[C:8]([O:10][C:11](=[O:13])[CH:12]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]=[CH:15][CH:16]=[CH2:17]>C1(C)C=CC=CC=1>[C:1]1([C:7]23[C:8](=[O:9])[O:10][C:11](=[O:13])[CH:12]2[CH2:14][CH:15]=[CH:16][CH2:17]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 99174Phenylmaleic anhydride

Product 1

HCID 126799041-Phenyl-4-cyclohexene-1,2-dicarboxylic acid anhydride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of α-phenyl-maleic anhydride (20 g, 0.115 moles), butadiene (40 g, 0.74 moles) and 200 ml of toluene was heated at 100° C. in a sealed bomb for 15 hrs. The toluene solution was decanted from an insoluble, polymeric material and evaporated in vacuo to yield crude 1-phenyl-4-cyclohexene-1,2-dicarboxylic acid anhydride, bp 155° (0.3 mm).

Workup

  1. customThe toluene solution was decanted from an insoluble, polymeric material
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-c37bfb081e7f41c9b948d30a2b36e182
Source dataset
uspto-grants-1977_08
Patent number
US04042707

Linked notes

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