Hydrochloric Acid → 4-Chlorovalerophenone

HRID 2058011Notes

Reaction equation

HRID 2058011 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-chlorovalerophenone 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-5cad96b9483c45d19b5722c0df764554
Source dataset
uspto-grants-1980_07
Patent number
US04213993

Reaction notes

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