Hydrochloric Acid → 4-Chloro-1-(5-chlorothiophen-2-yl)butan-1-one

HRID 2397859Notes

Reaction equation

HRID 2397859 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.Cl[CH:8]([CH2:12][CH3:13])[C:9](Cl)=[O:10].[Cl-:14].[Al+3].[Cl-].[Cl-].Cl>C(Cl)(Cl)(Cl)Cl>[Cl:14][CH2:13][CH2:12][CH2:8][C:9]([C:4]1[S:3][C:2]([Cl:1])=[CH:6][CH:5]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72992-ChlorothiopheneHCID 1390532-Chlorobutanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130916164-Chloro-1-(5-chlorothiophen-2-yl)butan-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirring solution of 59 g. (0.50 mole) 2-chlorothiophene, α-chlorobutyroylchloride and 500 ml. carbon tetrachloride maintained at 15°-25° C. with the aid of an ice bath was added portionwise 70.5 g. (0.60 mole) of aluminum chloride. The mixture was stirred at room temperature overnight and then carefully poured into 500 ml. of 20% hydrochloric acid solution. The organic layer was separated and washed with sodium bicarbonate solution followed by water. The organic solution was dried over (MgSO4), filtered, and concentrated to an oil under vacuum. The oil was distilled to give 82 g. of material which boiled at 140° C./2 mm. This material solidified on cooling.

Workup

  1. additionwas added portionwise 70.5 g
  2. additioncarefully poured into 500 ml
  3. customThe organic layer was separated
  4. washwashed with sodium bicarbonate solution
  5. dry with materialThe organic solution was dried over (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated to an oil under vacuum
  8. distillationThe oil was distilled
  9. customto give 82 g
  10. temperatureon cooling

Sources & evidence

ORD record
ord-de42b9433f1247f3878d469ff8a8b2ea
Source dataset
uspto-grants-1977_05
Patent number
US04022903

Reaction notes

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