Green synthesis of (-)-isopulegol from (+)-citronellal: Application to essential oil of citronella

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3605-3608

  Jacob, Raquel G ^a   Perin, Gelson ^a   Loi, Leticia N ^a   Pinno, Claudia S ^a   Lenardão, Eder J ^b  

^a UNIVERSIDADE REGIONAL DO NOROESTE DO ESTADO DO RIO GRANDE DO SUL   (Brazil)

^b FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

Isopulegol; Microwave; Solvent free reaction

Indexed keywords

ALCOHOL DERIVATIVE; CITRONELLAL; ISOPULEGOL; SILICON DERIVATIVE; UNCLASSIFIED DRUG; VEGETABLE OIL; ZINC CHLORIDE;

ARTICLE; BRAZIL; CATALYST; MICROWAVE IRRADIATION; PLANT; SOLID; SYNTHESIS;

CITRONELLA; CYMBOPOGON; CYMBOPOGON NARDUS; NARDUS;

EID: 0037471465     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00714-7     Document Type: Article

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21. 4 (1.2%; 9.88:0.12 g) by varying the Lewis acid and its amount.
22. 3) δ ( 2 ): 4.87 (m, 1H); 4.83 (s br, 1H); 3.43 (dt, J=10.4 and 4.3 Hz, 1H); 2.03 (m, 1H); 1.86 (m, 1H); 1.69 (d, J=0.5 Hz, 3H); 1.65 (m, 2H); 1.49 (m, 2H); 1.32 (m, 1H); 0.97 (m, 2H); 0.92 (d, J=6.5 Hz, 3H). ( 4 ): 3.67 (dt, J=10.4 and 4.2 Hz, 1H).
23. a Reunião Anual da Sociedade Brasileira de Química, Poços de Caldas, Brazil, 2002.
24. 2 (10%) (2.54 g; 40 mmol), essential oil of citronella (1.54 g; 40% of citronellal, determined by GC analysis) was added dropwise. The reaction mixture was irradiated at 427 W for 1.0 min, the reaction vessel was cooled at room temperature and the product was extracted from the silica gel with ethyl acetate (20 mL) and filtered. The solvent was evaporated under reduced pressure yielding a mixture of 2, 4 and 5 (ratio 2: 4: 5 =75:15:10) and other unreacted oil constituents.
25. The oven powers were determined according to: Kingston, H. M. In Introduction to Microwave Sample Preparation, Theory and Practice; Jassie, L. B., Ed.; American Chemical Society: Washington DC, 1988.