Hydrochloric Acid → 1-Acetyl-2,5-diisopropylbenzene

HRID 487359

Reaction equation

HRID 487359 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH:5]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[Cl-].[Cl-].[Cl-].[Al+3].Cl>C(=S)=S>[C:1]([C:12]1[CH:13]=[C:8]([CH:5]([CH3:6])[CH3:7])[CH:9]=[CH:10][C:11]=1[CH:14]([CH3:16])[CH3:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6367Acetyl chlorideHCID 74861,4-DiisopropylbenzeneHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 190947761-Acetyl-2,5-diisopropylbenzeneYield 88.5%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 142 ml (157 g, 2.0 mol) of acetyl chloride in 362 ml (310 g, 1.91 mol) of 1,4-diisopropylbenzene was added dropwise during the course of 2 hours to a suspension of 200 g (1.5 mol) of aluminum trichloride in 260 ml of carbon disulfide cooled to -10° C. The mixture was stirred for a further 1.5 hours at -100° C., in the course of which the evolution of hydrogen chloride greatly decreased, and a further 100 g (0.75 mol) of aluminum trichloride were then added in portions and the mixture was stirred for a further hour. The reaction mixture was cautiously poured onto I kg of ice/100 ml of 2N hydrochloric acid (strongly exothermic? ). The oily organic phase was separated off and the aqueous phase was extracted twice using ether. The combined organic phases were washed with dilute sodium carbonate solution, then with water and dried over calcium chloride. The solvents were stripped off and the residue was distilled through a 30 cm Vigreux column in a pump vacuum. After a forerun (b.p. 70°-91° C./ 0.6 torr, colorless oil, 10.9 g), the title compound (b.p. 92°-95° C./0.6 torr, colorless oil, 344.3 g, 1.69 mol), was obtained, yield 88.4%. The afterrun (b.p. 97°-104° C./1.0 torr, 10.25 g) is a colorless oil which immediately solidifies.

Workup

  1. customThe oily organic phase was separated off
  2. extractionthe aqueous phase was extracted twice using ether
  3. washThe combined organic phases were washed with dilute sodium carbonate solution
  4. dry with materialwith water and dried over calcium chloride
  5. distillationthe residue was distilled through a 30 cm Vigreux column in a pump vacuum

Sources & evidence

ORD record
ord-5a34d69891e346e0ad711931ec1c4246
Source dataset
uspto-grants-1994_03
Patent number
US05294724

Linked notes

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