Hydrochloric Acid → 4-Chlorovalerophenone

HRID 67139Notes

Reaction equation

HRID 67139 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Cl-:8].[Al+3].[Cl-].[Cl-].Cl.Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[Cl:8][CH:4]([CH3:5])[CH2:3][CH2:2][C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 61186Valeryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 144729704-Chlorovalerophenone

Procedure

A mixture of 346 ml of chlorobenzene and 120 g of valeryl chloride is treated, at room temperature, in the course of 1 hour with portions of aluminium chloride and the mixture is at the same time heated to 70°. The mixture is stirred for a further hour at this temperature and then cooled to 25° and the dark red reaction mixture is poured on to 1,000 g of ice. Concentrated hydrochloric acid is added and the mixture is then extracted with ethyl acetate. The organic extract is washed with 2 N hydrochloric acid, filtered through a diatomaceous earth formulation (Hyflo) and washed with further 2 N hydrochloric acid, twice with water with a 2 N aqueous solution of sodium carbonate and with water. It is dried over sodium sulphate and filtered and the filtrate is evaporated under reduced pressure. The residue is distilled; 4-chloro-valerophenone is obtained at 155°-156°/14 mm Hg; the product crystallises and melts at 28°-30°.

Workup

  1. temperatureheated to 70°
  2. temperaturecooled to 25°
  3. customthe dark red reaction mixture
  4. extractionthe mixture is then extracted with ethyl acetate
  5. extractionThe organic extract
  6. washis washed with 2 N hydrochloric acid
  7. filtrationfiltered through a diatomaceous earth formulation (Hyflo)
  8. washwashed with further 2 N hydrochloric acid, twice with water with a 2 N aqueous solution of sodium carbonate and with water
  9. dry with materialIt is dried over sodium sulphate
  10. filtrationfiltered
  11. customthe filtrate is evaporated under reduced pressure
  12. distillationThe residue is distilled

Sources & evidence

ORD record
ord-b06bf5b5636549808aa1d1ebb8213f7a
Source dataset
uspto-grants-1982_08
Patent number
US04344957

Reaction notes

Loading…