Highly efficient dithioacetalization of carbonyl compounds catalyzed with iodine supported on neutral alumina

Chemistry Letters

Volumn , Issue 8, 2001, Pages 794-795

  Deka, Nabajyoti ^a   Sarma, Jadab C ^a,b  

^a REGIONAL RESEARCH LABORATORY   (India)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035538660     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.794     Document Type: Article

References (27)

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19. Procedure for preparation of the catalyst: The catalyst was prepared by making a slurry of activated neutral alumina (1 g, Aldrich, standard grade, 150 mesh) with a solution of 51 mg (0.20 mmol) of iodine in 2 mL of dichloromethane. The slurry was stirred magnetically at room temperature for 30 minutes and the excess solvent was removed by evaporation under reduced pressure and at low temperature. When the slurry became dry and free falling it was ready for use.
20. Typical procedure for dithioacetalization: To a freshly prepared catalyst (1 g, 0.2 mmol of iodine) under stirring, a mixture of benzaldehyde (2 mmol) and ethane-1,2-dithiol (2.2 mmol) was added and stirring continued for 10 min or till the reaction was complete. For TLC monitoring, a small amount of the solid reaction mixture was taken out with a spatula and washed with a little amount of ethyl acetate to get a solution. On completion the reaction mixture was loaded on a short column of silica gel (60 to 120 mesh) and eluted with ethyl acetate. The organic layer was washed with a dilute solution of sodium thiosulfate followed by water and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure and purification of the residue by coloumn chromatography yielded the pure product.
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25. 2: C, 68.28; H, 11.46; S, 20.25%. Found: C, 68.27; H, 11.73; S, 20.08%.
26. 2: C, 67.11; H, 9.01; S, 23.89%. Found: C, 67.57; H, 9.08; S, 23.24%.
27. 2: C, 61.86; H, 6.39; O, 6.34; S, 25.41%. Found: C, 61.32; H, 6.44; S, 25.86%.