Chlorobenzene → 5465-37-2

HRID 1903900Notes

Reaction equation

HRID 1903900 reaction equation
[Cl-:1].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:11])/[CH:6]=[CH:7]/[C:8](Cl)=[O:9].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:5](/[CH:6]=[CH:7]/[C:8](=[O:9])[C:14]2[CH:19]=[CH:18][C:17]([Cl:1])=[CH:16][CH:15]=2)=[O:11])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 5325504Fumaryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14847845465-37-2

Conditions

Temperature
45 °C

Procedure

To a stirred suspension of 31 gm (0.23 mol) of aluminum trichloride in 230 ml chlorobenzene, 18 gm (0.12 mol) of fumaryl chloride were added slowly in drops at room temperature. The mixture was stirred for 1.3 hours at room temperature and for another 1.3 hours at 45° C. After introduction into ice-water and acidification with concentrated HCl, the mixture was extracted with 1.5 liters of methylene chloride. After evaporation of the methylene chloride, the residue was washed with about 200 ml of ethanol and recrystallized from acetone. 27 gm (75% of the theory) of trans-1,2-bis-(p-chlorobenzoyl)-ethene were obtained with a melting point of 174°-176° C.

Workup

  1. additionwere added slowly in drops at room temperature
  2. extractionAfter introduction into ice-water and acidification with concentrated HCl, the mixture was extracted with 1.5 liters of methylene chloride
  3. customAfter evaporation of the methylene chloride
  4. washthe residue was washed with about 200 ml of ethanol
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-2d17cc918ac045eb8df08f383e7982fc
Source dataset
uspto-grants-1984_03
Patent number
US04439418

Reaction notes

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