Hydrochloric Acid → p-tert-Butylacetophenone

HRID 1764075Notes

Reaction equation

HRID 1764075 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].Cl>O.C(Cl)(Cl)(Cl)Cl>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:5](=[O:7])[CH3:6])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 7366Tert-ButylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13669p-tert-ButylacetophenoneYield 97.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

514 grams (3.85 mol) of anhydrous aluminum chloride was put into 2 liters of carbon tetrachloride. While stirring vigorously, 302 grams (3.85 mol) of acetylchloride was added over a period of 1 hour at a temperature below 10° C. Subsequently, 469 grams (3.5 mol) of tert.butylbenzene was added to the reaction mixture over a period of 3 hours at a temperature below 5° C. After stirring for 1 hour without cooling, the reaction mixture was poured into a mixture of 500 milliliters of water, 1.7 kilograms of ice and 150 milliliters of 35% hydrochloric acid. The organic phase was separated, washed to neutrality and dried. After the solvent had been distilled off, 600 grams of 4'-tert.butylacetophenone was obtained having a refractive index nD20 = 1.5212. 444 grams (2.02 mol) of the above-described 4'-tert.butylacetophenone was mixed with 1.25 liters of glacial acetic acid and heated to 60° C. while stirring. Subsequently, at a reaction temperature of about 60° C., 375 grams (5.28 mol) of gaseous chlorine was passed into the reaction mixture for 41/2 hours. After the reaction mixture had been freed from hydrogen chloride gas and the excess of chlorine by passing through nitrogen, 414 grams (5.05 mol) of anhydrous sodium acetate was added and then the reaction mixture was heated to 95° C. Subsequently, another 185 grams (2.60 mol) of gaseous chlorine was passed into the reaction mixture for 2 hours at a temperature of about 95° C. The excess of chlorine was again removed with the aid of nitrogen and then the hot reaction mixture was filtered. After the addition of 63 milliliters of water, the clear filtrate was cooled to room temperature, which caused 2,2,2-trichloro-4'-tert.butylacetophenone to crystallize out. After filtering off by suction, washing and drying, 530 grams of white crystalline final product was obtained, having a melting point of 61.5° - 62.5° C.

Workup

  1. stirringAfter stirring for 1 hour
  2. temperaturewithout cooling
  3. customThe organic phase was separated
  4. washwashed to neutrality
  5. customdried
  6. distillationAfter the solvent had been distilled off

Sources & evidence

ORD record
ord-00adaae5a82c4bd897e1a8678252eb51
Source dataset
uspto-grants-1978_09
Patent number
US04115224

Reaction notes

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