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

HRID 2398768Notes

Reaction equation

HRID 2398768 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

Dibenzothiophene (18.4g.) and anhydrous aluminium chloride (13.3g.) were mechanically stirred in carbon disulphide (100 ml.) while acetyl chloride (7.85g.) 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.

Workup

  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

Sources & evidence

ORD record
ord-c046e91861f948f7a190bfa5eef1eaf6
Source dataset
uspto-grants-1977_05
Patent number
US04025635

Reaction notes

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