Maleic Anhydride → 4,5-Dichlorotetrahydrophthalic anhydride

HRID 345958

Reaction equation

HRID 345958 reaction equation
[Cl:1][C:2]([C:4]([Cl:6])=[CH2:5])=[CH2:3].[C:7]1(=[O:13])[O:12][C:10](=[O:11])[CH:9]=[CH:8]1>C1(C)C=CC=CC=1>[Cl:1][CH:2]1[C:4]([Cl:6])=[CH:5][CH:9]2[C:10]([O:12][C:7](=[O:13])[CH:8]2[CH2:3]1)=[O:11]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 154472,3-Dichloro-1,3-butadiene

Product 1

HCID 541398954,5-Dichlorotetrahydrophthalic anhydrideYield 61.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 500 mL reaction flask was charged with 34.5 g of 2,3-dichlorobutadiene and 27.5 g of maleic anhydride. 200 mL of toluene was added, along with a small amount of BHT (0.5 g). The solution was heated to reflux until the reaction was complete. The toluene was removed and the product recrystallized from ethyl acetate/hexanes to give 38.25 g (61.8%) of 4,5-dichlorotetrahydrophthalic anhydride.

Workup

  1. customA 500 mL reaction flask
  2. temperatureThe solution was heated
  3. temperatureto reflux until the reaction
  4. customThe toluene was removed
  5. customthe product recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-97799dd1ebef4fde987c5935e4a800db
Source dataset
uspto-grants-1991_10
Patent number
US05059697

Linked notes

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