Benzene → Succinic anhydride

HRID 444119Notes

Reaction equation

HRID 444119 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[C]=O.[CH:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:10]1([C:2]2[C:1]([O:6][C:4](=[O:5])[CH:3]=2)=[O:7])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:4]1(=[O:5])[O:6][C:1](=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 7923Maleic AnhydrideHCID 178418416HCID 178418416, compound

Product 2

HCID 7922Succinic anhydrideHCID 99174Phenylmaleic anhydride

Conditions

Temperature
220 °C

Procedure

In the same autoclave as used in Example 1, 50 ml of benzene, 0.98 g of maleic anhydride and 0.019 g of Rh4 (CO)12 were charged, followed by supply of carbon monoxide under 30 kg/cm2. The charge in the autoclave was heated at 220° C. for 7 hours. The reaction mixture was cooled and benzene was removed by distillation under reduced pressure. The residue was separated by silica column chromatography to obtain 0.363 g of phenylmaleic anhydride and 0.136 g of succinic anhydride. Each product was identified based on the infrared absorption spectrum (hereinafter referred to as "IR") of the standard substance and the retention time in GC.

Workup

  1. additionwere charged
  2. additionThe charge in the autoclave
  3. temperatureThe reaction mixture was cooled
  4. custombenzene was removed by distillation under reduced pressure
  5. customThe residue was separated by silica column chromatography

Sources & evidence

ORD record
ord-0c2c820f5d364803a58965d922934711
Source dataset
uspto-grants-1981_04
Patent number
US04263212

Reaction notes

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