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

HRID 614493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614493
[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-].[C:18](Cl)(=[O:20])[CH3:19]>C(=S)=S>[C:18]([C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=1)(=[O:20])[CH3:19]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel2×

Versuchsvorschrift

Dibenzothiophene (18.4g.) and anhydrous aluminium chloride (13.3 g.) were mechanically stirred in carbon disulphide (100 ml.) while acetyl chloride (7.85 g.) in carbon disulphide (20 ml.) was added dropwise over 0.5 hr. The temperature of the mixture rose to 30° C. After a total of 4 hr. stirring the mixture was poured on to ice and extracted with chloroform. The extract was washed with sodium bicarbonate solution, dried with magnesium sulphate, and evaporated. The residue was distilled under vacuum and a fraction, b.pt. 160°-180° C. at 0.6 mm. Hg was extracted by boiling with ether, and the residue recrystallised twice from methanol to give colourless crystals of 2-acetyldibenzothiophene m.pt. 97°-100° C.

Aufarbeitung

  1. additionwas added dropwise over 0.5 hr
  2. customrose to 30° C
  3. customAfter a total of 4 hr
  4. additionwas poured on to ice
  5. extractionextracted with chloroform
  6. washThe extract was washed with sodium bicarbonate solution
  7. dry with materialdried with magnesium sulphate
  8. customevaporated
  9. distillationThe residue was distilled under vacuum
  10. extractiona fraction, b.pt. 160°-180° C. at 0.6 mm. Hg was extracted
  11. customthe residue recrystallised twice from methanol

Quellen und Nachweise

ORD-Eintrag
ord-c71daf471eaa4a09b9b84aabfdc224e8
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04145350

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