An Economically Viable Route to Cis/Trans-(±)-2, 2-dimethyl-3-(2′,2′-dichlorovinyl)Cyclopropane Carboxylic Acid Esters

References

• Elliot , M. and Jane , N. F. 1973 . Pyrethrum, The Natural Insecticide , Edited by: Casida , J. E. 55 – 100 . New York : Academic Press . For reviews, See
   Google Scholar
• Elliot , M. 1977 . Synthetic Pyrethroids , A.C.S. Symposium Series 42 Washington, DC : American Chemical Society .
   Google Scholar
• Janes , N. F. 1985 . Recent Advances in the Chemistry of Insect Control , London : The Royal Society of Chemistry . Special Publication No. 53
   Google Scholar
• Mandal , A. K , Borude , D. P. , Armugaswamy , R. , Soni , N. R. , Jawalkar , D. G. , Mahajan , S. W. , Ratnam , K. R. and Ghogare , A. D. 1986 . Tetrahedron. , 42 : 5715
   Web of Science ®Google Scholar
• Bevinakatti , H. S. , Newadkar , R. V. , Borude , D. P. and Mandal , A. K. 1988 . J. Org. Chem. , 53 : 3843
   Google Scholar
• Mandal , A. K. and Borude , D. P. Indian Patent Application No., 346/Cal . 1990 .
   Google Scholar
• The lactones 7b and 7a are obtained by the chlorination of the haloacids 6b (90%) and 6a (10%). This composition did not change even with excess chlorine
   Google Scholar
• Pizey , J. S. 1981 . “Synthetic Reagents” , Vol. 4 , 353 – 360 . New York : John Wiley & Sons .
   Google Scholar
• Vehre , R. and De Kimpe , N. 1983 . “The Chemistry of Functional Groups, Supplement D” , Edited by: Patai , S. and Rappapap , Z. 820 – 824 . New York : John Wiley . eqn. 19 & eqn. 26 Pt 1
   Google Scholar
• The chlorination of the lactone, 5a with these reagents under similar conditions, however, furnished 5a as the sole product, ref. 3
   Google Scholar
• Arlt , D. , Jantelat , M. and Lantzsch , R. 1981 . Angew. Chem. Int., Ed. English , 20 : 709 – 710 . and references cited therein.
   Google Scholar
• Based on our experience, oxidation with sodium dichromate is cheaper than potassium permanganate due to cost advantage and better raw material usage in the former case. In the present case, of the 178.8 g of sodium dichromate required for the oxidation of 46.2 g of 7, the contribution of chromium is 64.0 g which is further lowered by ∼ 20% during scale-up due to better process control. Hence the usage requirement of chromium per ketone would be ∼1:1. For effluent treatment, the aqueous layer was treated with sulphur dioxide to convert higher valent chromium, if any, to Cr (III) which is then precipitated by treatment with lime. The precipitated salt is then filtered and the aqueous layer is then tested for the permissible level of chromium, subjected to charcoal treatment, aerial oxidation etc, diluted and then discharged.
   Google Scholar
• Wasson , R. L. and House , H. O. 1963 . Org. Synth. Coll. Vol. 4 , 552
   Google Scholar