As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO35,mainly used in chemical industry, its synthesis route is as follows.,14098-24-9
Concentrated nitric acid (0.25 ml) was added to a stirring solution of benzo-18-crown-6 (12) (0.25 g, 0.81 mmol) in dichloromethane (15 ml). The solution was allowed to stir at room temperature for 24 hours. The organic layer was washed with water (3 x 30 ml), dried over sodium sulfate, filtered and the solvent removed under reduced pressure. The isolated oily product solidified upon standing to give 0.28 g of (13) as a yellow crystalline solid (0.78 mmol, 96 % yield). 1H n. m. r. of the crude indicated the presence of product and also dichloromethane. The product was allowed to dry for another 24 hours before its employment in subsequent reactions. Melting point: 82-83 C (Literature mp: 80-81 C)31. Decompostion at: 312 C. 1H n. m. r. (300 MHz, CDCl3): delta 7.88 (dd, 1H, J 8.9 Hz, 2.6 Hz, Ar-H); 7.74 (d, 1 H, J 2.6 Hz, Ar-H); 6.89 (d, 1 H, J 8.9 Hz, Ar-H); 4.24 (m, 4H, OCH2); 3.95 (m, 4H, OCH2); 3.77 (m, 4H, OCH2); 3.72 (m, 4H, OCH2); 3.68 (s, 4H, OCH2). 13C n. m. r. (75 MHz, CDCl3): delta 154.3, (C4); 148.4, (C2); 141.3, (C1); 117.9, (C5); 111.2, (C6); 108.1, (C3); 70.99, (OCH2); 70.98, (OCH2); 70.8, (OCH2); 70.7, (OCH2); 70.60, (OCH2); 70. 57, (OCH2); 69.23, (OCH2); 69.17, (OCH2); 69.1, (OCH2). IR (Nujol): 1587, m; 1520, s; 1464, s; 1338, s; 1276, s; 1128, s; 864, w. Mass spectrum (ESI,+ve): m/z 358.1 [M]+; 381.1 [M + Na]+.
With the synthetic route has been constantly updated, we look forward to future research findings about Benzo-18-crown 6-Ether,belong chiral-catalyst compound
Reference£º
Patent; Monash University; WO2003/99762; (2003); A1;,
Chiral Catalysts
Chiral catalysts – SlideShare