1,2-Dichloroethane → 4-Chloro-4'-nitrobenzophenone

HRID 1778209Notes

Reaction equation

HRID 1778209 reaction equation
ClCCCl.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)([O-:14])=[O:13].[Cl-].[Cl-].[Cl-].[Al+3]>CCO>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:19]([C:18]2[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:23][CH:22]=2)=[O:20])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7964ChlorobenzeneHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3477714-Chloro-4'-nitrobenzophenone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A 2-L 4-neck flask equipped with a thermocouple controller, a mechanical stirrer, a condenser, and a nitrogen inlet/outlet adapter was charged with DCE (480.8 mL), chlorobenzene (1) (90.4 mL, 888.5 mmol) and 4-nitrobenzoylchloride (111.4 g, 600.3 mmol), and the resulting mixture stirred and warmed to 40° C. Aluminum trichloride (97.0 g, 720.4 mmol) was added portionwise over 1 h and then the reaction was heated to 60° C. and stirred for 10 h. The reaction was cooled to 20° C., poured into ice-water (2 L) and stirred for 10 min. The resulting aqueous mixture was extracted with DCM (600 mL×2). The combined organic extracts were was washed with deionized water (1 L×3). The solvent was concentrated at 40° C. to remove DCM and then at 66° C. to yield a pale to slight yellowish solid, which was dissolved in hot EtOH (500 mL) at 76° C., stirred for 30 min, and then gradually cooled to 4° C. over 1 h. The resulting solid was collected by filtration to yield (4-chlorophenyl)(4-nitrophenyl)methanone as a slightly yellowish crystalline solid. (ES, m/z) 262 (M+H)+, 284, 286 (M+Na)+

Workup

  1. customA 2-L 4-neck flask equipped with a thermocouple controller, a mechanical stirrer, a condenser, and a nitrogen inlet/outlet adapter
  2. temperaturethe reaction was heated to 60° C.
  3. stirringstirred for 10 h
  4. temperatureThe reaction was cooled to 20° C.
  5. stirringstirred for 10 min
  6. extractionThe resulting aqueous mixture was extracted with DCM (600 mL×2)
  7. washThe combined organic extracts were was washed with deionized water (1 L×3)
  8. concentrationThe solvent was concentrated at 40° C.
  9. customto remove DCM
  10. customat 66° C. to yield a pale to slight yellowish solid, which
  11. stirringstirred for 30 min
  12. temperaturegradually cooled to 4° C. over 1 h
  13. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-07b8f3ec096044d8985b17500fddd97f
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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