Hydrochloric Acid → 4'-Bromovalerophenone

HRID 1788617Notes

Reaction equation

HRID 1788617 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(=S)=S>[C:5]([C:16]1[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][CH:15]=1)(=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 61186Valeryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 817174'-BromovalerophenoneYield 61.6%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
0 °C

Procedure

104.5 g (0.76 mol) of anhydrous aluminum chloride and 92.1 g (0.76 mol) of valeroylchloride were added to 350 ml of carbon disulfide chilled at 0° C. To the resulting mixture with chilling and stirring, 100 g (0.64 mol) of bromobenzene was added and the solution was stirred at room temperature for 24 hours. After completion of the reaction, the resulting mixture was added to 400 ml of cold 4N hydrochloric acid and the aluminum chloride complex was decomposed. Then the organic layer was extracted with chloroform and washed with water and the solvent was removed by distillation. The residue was distilled under reduced pressure to yield 95 g of 4-pentanoylbromobenzene having a b.p. 105° to 110° C./2 mmGn.

Workup

  1. temperatureTo the resulting mixture with chilling
  2. stirringthe solution was stirred at room temperature for 24 hours
  3. customAfter completion of the reaction
  4. extractionThen the organic layer was extracted with chloroform
  5. washwashed with water
  6. customthe solvent was removed by distillation
  7. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-0c3e91422e8b4735b26950b5d98d588a
Source dataset
uspto-grants-1987_08
Patent number
US04684220

Reaction notes

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