Hydrochloric Acid → 4'-Bromovalerophenone

HRID 1638278Notes

Reaction equation

HRID 1638278 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'-Bromovalerophenone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
0 °C

Procedure

104.5g (0.76mol) of anhydrous aluminum chloride and 92.1g (0.76mol) of valeroylchloride were added to 350ml of carbon disulfide chilled at 0° C. To the resulting mixture with chilling and stirring, 100g (0.64mol) 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 400ml 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 95g of 4-pentanoylbromobenzene having a b.p. 105° to 110° C./2mmGn.

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-e058321dc84845488d03abf1a4dcfb93
Source dataset
uspto-grants-1989_11
Patent number
US04879060

Reaction notes

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