Hydrochloric Acid → 4'-Chloro-2-(4-tert-butylphenyl)acetophenone

HRID 1975652Notes

Reaction equation

HRID 1975652 reaction equation
II.Br[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]#N)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].Cl.C([O:27]CC)C>>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:22](=[O:27])[CH2:21][C:18]2[CH:19]=[CH:20][C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:16][CH:17]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 3283Diethyl Ether3×HCID 7806p-BromochlorobenzeneHCID 76784(4-tert-Butylphenyl)acetonitrile

Product 1

HCID 190982304'-Chloro-2-(4-tert-butylphenyl)acetophenone

Procedure

0.7 of magnesium(scraped shape) and 100 mg of a chip of iodine were added to 5 ml of anhydrous diethyl ether. 10 ml of anhydrous diethyl ether solution of 5.6 g of p-bromochlorobenzene was dropwise added thereto under nitrogen stream at a rate that was just fast enough to maintain a gentle reflux. This solution was stirred at room temperature for 20 minutes to react them, a solution of 4.8 g of p-tert-butylphenyl acetonitrile in 5 ml of anhydrous diethyl ether was dropwise added thereto at a rate that was just fast enough to maintain a gentle reflux. The solution was further stirred for 30 minutes to react them. After completion of the reaction, a mixture solution of 10 g of ice and 130 ml of 6N-hydrochloric acid was added thereto and a reaction product was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The redisue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9) to obtain 1.3 g of 4'-chloro-2-(4-tert-butylphenyl)acetophenone. (2) 1.3 g of (4.5 mmol) of 4'-chloro-2-(4-tert-butylphenyl)acetophenone was dissolved in 15 ml of ethanol, and 0.2 g (4.5 mmol) of hydrazine monohydrate was added thereto. The mixture was refluxed under heating for three hours. After completion of the reaction, ethanol was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 1.3 g of [4'-chloro-2-(4-tert-butylphenyl)acetophenone]hydrazone as a yellow oily substance.

Workup

  1. temperatureto maintain a gentle reflux
  2. customto react them
  3. temperatureto maintain a gentle reflux
  4. stirringThe solution was further stirred for 30 minutes
  5. customto react them
  6. customAfter completion of the reaction
  7. extractiona reaction product was extracted with ethyl acetate
  8. washThe extract was washed with water
  9. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe redisue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/9)

Sources & evidence

ORD record
ord-571261998dca4bcd9aa28d2b8e985eb8
Source dataset
uspto-grants-1994_02
Patent number
US05288727

Reaction notes

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