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Facile synthesis of optical pure fenoxaprop-p-ethyl[ethyl (R)-2-{4-(chloro-1,3-benzoxazol-2-yloxy)phenoxy}propionate]  

Ryu, Sung-Kon (Korea Research Institute of Chemical Technology)
Ko, Young-Kwan (Korea Research Institute of Chemical Technology)
Chang, Hae-Sung (Korea Research Institute of Chemical Technology)
Ryu, Jae-Wook (Korea Research Institute of Chemical Technology)
Woo, Jae-Chun (Korea Research Institute of Chemical Technology)
Koo, Dong-Wan (Korea Research Institute of Chemical Technology)
Kim, Dae-Whang (Korea Research Institute of Chemical Technology)
Chung, Kun-Hoe (Korea Research Institute of Chemical Technology)
Publication Information
The Korean Journal of Pesticide Science / v.8, no.1, 2004 , pp. 1-7 More about this Journal
Abstract
Fenoxaprop-p-ethyl[Ethyl (R)-2-{4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy}propionate] is well known as a herbicide for its specific activity against the weed grasses. This compound was synthesized by the reaction of 4-(6-chloro-1,3-benzoxazol-2-yloxy)phenol and ethyl (S)-O-(p-toluenesulfonyl)lactate in good yields with high optical pure(optical purity: 99.9% up). In this process Walden inversion occurs, whereby the S-configuration of the propionic acid derivative is converted to the R-configuration of the final product. 4-(6-Chloro-l,3-benzoxazol-2-yloxy)phenol was obtained by 5 step reactions in over-all 70% yields using inexpensive raw materials.
Keywords
fenoxaprop-p-ethyl; ethyl (S)-O-(p-toluenesulfonyl)lactate; 2,6-dichloro-1,3-benzoxazole; (6-chloro-1,3-benzoxazol-2-yloxy)phenol; herbicide;
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