Toluene → HCID 54187688, compound

HRID 1860274Notes

Reaction equation

HRID 1860274 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.C1(C)C=CC=CC=1.[CH2:15]=[CH:16][C:17]([Cl:19])=[CH2:18]>C1(C)C(C)=CC=CC=1>[Cl:19][CH:17]1[CH:16]=[CH:15][CH:2]2[C:1]([O:6][C:4](=[O:5])[CH:3]2[CH2:18]1)=[O:7]

Participants

5

Reactant 3

HCID 1140TolueneHCID 7923Maleic AnhydrideHCID 31369Chloroprene

Product 1

HCID 54187688HCID 54187688, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
55 °C

Procedure

156.9 g (1.6 mole) of maleic anhydride and 250 ml toluene were added to a flask. 25 ml of toluene was removed by distillation to dry the solution. 150 g (1.69 mole) of chloroprene dissolved in 250 ml of xylene was slowly added to the flask. The entire addition took 30 minutes. The resulting solution was then heated at 55° C. for three hours. The solution was then distilled to remove solvents. The remaining material was distilled at 160-165° C. (1 to 2 mm pressure) to afford 4-chlorotetrahydrophthalic anhydride in 85% yield (253 grams).

Workup

  1. custom25 ml of toluene was removed by distillation
  2. customto dry the solution
  3. additionwas slowly added to the flask
  4. additionThe entire addition
  5. distillationThe solution was then distilled
  6. customto remove solvents
  7. distillationThe remaining material was distilled at 160-165° C. (1 to 2 mm pressure)

Sources & evidence

ORD record
ord-1dc5030387764393911c98c104b87fc2
Source dataset
uspto-grants-2003_03
Patent number
US06528663B1

Reaction notes

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