Mono-6-O-(p-toluenesulfonyl)-beta-cyclodextrin

Uses

Mono(6-O-p-tolylsulfonyl)-β-cyclodextrin (CAS# 67217-55-4) is carbohydrate used in the preparation of electroactive polyaniline/silica hybrid sol-gels. Recently, mono(6-O-p-tolylsulfonyl)-β-cyclodextrin has been proposed for use as a catalyst for atmospheric CO2 fixation by conversion to cuclic carbonate.

Synthesis

The general procedure for the synthesis of mono-6-O-(p-toluenesulfonyl)-β-cyclodextrin from 1-(p-toluenesulfonyl)imidazole and β-cyclodextrin was as follows: in a 1L two-necked round-bottomed flask, β-cyclodextrin (40.0 g, 35.2 mmol) was dissolved in 450 mL of deionized water at 60°C with vigorous stirring until complete dissolution. To the resulting emulsion suspension was added 1-(p-toluenesulfonyl)-imidazole (12 g, 54 mmol). After the reaction mixture was stirred for 2 hours, a 25 mL aqueous solution of sodium hydroxide (9 g, 225 mmol) was slowly added (about 20 minutes to complete the drop). After continued stirring for 20 minutes, unreacted 1-(p-toluenesulfonyl)-imidazole was removed by filtration through a sintered glass funnel. Subsequently, ammonium chloride (24.1 g, 900 mmol) was added to the reaction solution to quench the reaction and all solids were dissolved by rotary evaporation. The reaction mixture was concentrated to half the original volume by blowing a stream of air over its surface. The resulting suspension was filtered through a large sintered glass funnel and the collected solids were washed sequentially with ice water (2 x 100 mL) and acetone (1 x 200 mL), and finally dried in a vacuum desiccator with CaCl2 as the drying agent to constant weight. The product 20.63 g was obtained in 45.39% (16 mmol) yield.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 25, p. 3268 - 3273
[2] Synthetic Communications, 2014, vol. 44, # 5, p. 589 - 599
[3] Green Chemistry, 2014, vol. 16, # 6, p. 3117 - 3124
[4] Carbohydrate Research, 2016, vol. 430, p. 85 - 94
[5] Organic Syntheses, 2000, vol. 77, p. 225 - 225