Dehydrative amination of alcohols in water using a water-soluble calix[4]resorcinarene sulfonic acid

Synlett

Volumn , Issue 10, 2008, Pages 1539-1542

  Shirakawa, Seiji ^a   Shimizu, Shoichi ^a  

^a Department of Industrial Chemistry   (Japan)

Author keywords

Animations; Calixarenes; Green chemistry; Host guest systems; Phase transfer catalysis

Indexed keywords

ALCOHOL DERIVATIVE; CALIX[4]RESORCINARENE SULFONIC ACID; SULFONIC ACID DERIVATIVE; WATER;

AMINATION; ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 46449096605     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/S-2008-1078416     Document Type: Article

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61. General Experimental Procedure for Dehydrative Amination in H2O (Table 2): Alcohol (0.30 mmol) andp-toluenesulfonamide (0.45 mmol) were added to a solution of water-soluble calix[4]resorcinarene sulfonic acid I1320 (0.030 mmol) in H2O (1 mL) with stirring, and the reaction mixture was vigorously stirred at 60°C for an additional 24 h. After the addition of sat. aq NaHCO3 solution (3 mL), the resulting mixture was extracted with EtOAc (3×3 mL). The combined extracts were dried over anhyd Na2SO4 and evaporated. The products were purified by flash chromatography on silica gel to yield the amination product. Recycling Experiments (Table 3): Alcohol (0.90 mmol) and/7-toluenesulfonamide (1.08 mmol) were added to a solution of water-soluble calix[4]resorcinarene sulfonic acid 1 (0.090 mmol) in H2O (3 mL) with stirring, and the reaction mixture was vigorously stirred at 60°C for an additional 24 h. After each reaction, EtOAc (3 mL) was added to the reaction mixture, and the solution was stirred for 5 min. The resulting mixture was allowed to stand for 5 min and then the organic phase was removed via a syringe. This extraction procedure was repeated twice. The remaining aqueous catalyst solution was reused directly in the next cycle. Isolation of the amination product 2a was performed in a manner similar to that described above.
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