Hydrochloric Acid → 4'-Bromovalerophenone

HRID 327362Notes

Reaction equation

HRID 327362 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Cl-].[Al+3].[Cl-].[Cl-].Cl.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:1]([C:17]1[CH:18]=[CH:19][C:14]([Br:13])=[CH:15][CH:16]=1)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 4

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

Product 1

HCID 817174'-Bromovalerophenone

Conditions

Temperature
0 °C

Procedure

Pentanoyl chloride (50 g) is added dropwise to a stirred, cooled 0° C.) mixture of bromobenzene (150 ml) and aluminum chloride (0.2 g). The mixture is stirred at 0° C. for 1 h, heated at 80° C. for 2 h, cooled and poured into 18% hydrochloric acid. The product is extracted into CHCl3 twice, the combined organic extracts are washed with water and steam distilled to remove chloroform and the excess of bromobenzene. The product is extracted into chloroform twice, the combined organic phases are washed with water and dried (MgSO4). The solvent is removed in vacuo and the residue is distilled (bp 180°-184° C. at 20 mm Hg) to yield a colourless solid.

Workup

  1. temperatureheated at 80° C. for 2 h
  2. temperaturecooled
  3. extractionThe product is extracted into CHCl3 twice
  4. washthe combined organic extracts are washed with water and steam
  5. distillationdistilled
  6. customto remove chloroform
  7. extractionThe product is extracted into chloroform twice
  8. washthe combined organic phases are washed with water
  9. dry with materialdried (MgSO4)
  10. customThe solvent is removed in vacuo
  11. distillationthe residue is distilled (bp 180°-184° C. at 20 mm Hg)
  12. customto yield a colourless solid

Sources & evidence

ORD record
ord-4061ac3f1088450d898ceb7529f029fe
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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