4-Chlorobenzoyl chloride → HCID 19883675, compound

HRID 846714Notes

Reaction equation

HRID 846714 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:14][CH:13]=2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 5224107-Phenyl-1-heptyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19883675HCID 19883675, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

1.07 g of 7-chloroheptylbenzene and 0.89 g of 4-chlorobenzoyl chloride were dissolved in 10 ml of nitrobenzene and treated with 0.82 g of aluminium chloride under argon and while cooling with ice. The mixture was then stirred at room temperature for 18 hours, taken up in 100 ml of ice-cold 2N hydrochloric acid solution and extracted three times with 50 ml of ether each time. The organic phases were washed with 50 ml of a 10 percent sodium bicarbonate solution and 50 ml of a saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The nitrobenzene was removed by distillation at 80°-100° C. and 20 Pa. By distillation at 240°-250° C. and about 13.4 Pa there were obtained 1.32 g (74%) of 4-chloro-4'-(7-chloroheptyl)benzophenone as a light yellow oil.

Workup

  1. temperaturewhile cooling with ice
  2. extractionextracted three times with 50 ml of ether each time
  3. washThe organic phases were washed with 50 ml of a 10 percent sodium bicarbonate solution and 50 ml of a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe nitrobenzene was removed by distillation at 80°-100° C.
  7. distillationBy distillation at 240°-250° C.

Sources & evidence

ORD record
ord-186bfe639a67481aae1a7daa1a88b54e
Source dataset
uspto-grants-1992_08
Patent number
US05137920

Reaction notes

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