Hydrochloric Acid → 1-(Dibenzo[b,d]thiophen-2-yl)ethan-1-one

HRID 1089183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089183
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:19]([CH3:20])=[O:21]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3023DibenzothiopheneHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 3120271-(Dibenzo[b,d]thiophen-2-yl)ethan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943Carbon TetrachlorideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 147.4 g of dibenzothiophene in 1.6 liters of carbon tetrachloride, cooled in an ice bath, was added a filtered solution of 122.7 g of anhydrous aluminum chloride in 425 ml of dichloromethane and 65.4 ml of acetyl chloride at 10° C., over 45 minutes. The mixture was stirred for 20 minutes, then a mixture of 2.5 liters of crushed ice and 500 ml of concentrated hydrochloric acid was added in one portion. This mixture was stirred vigorously until the yellow color disappeared. The aqueous layer was separated and washed in 100 ml of carbon tetrachloride. The wash was combined with the organic layer, washed with two 2 liter portions of water, dried and evaporated. The residue was crystallized from 250 ml of toluene and 750 ml of ether, giving 85.9 g of the desired product as colorless crystals, mp 107°-110° C.

Aufarbeitung

  1. additionwas added in one portion
  2. stirringThis mixture was stirred vigorously until the yellow color
  3. customThe aqueous layer was separated
  4. washwashed in 100 ml of carbon tetrachloride
  5. washwashed with two 2 liter portions of water
  6. customdried
  7. customevaporated
  8. customThe residue was crystallized from 250 ml of toluene and 750 ml of ether

Quellen und Nachweise

ORD-Eintrag
ord-c6048bc4716741e68ab388f9241e3f78
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04965284

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