Regioselective Synthesis of 2,3-Dichloroprop-1-ene from 1,2,3-Trichloropropane and Its Synthetic Transformations

Page: 575

J. Sauliova, B. Hiklova a P. Zustakova

Department of Chemistry, Pedagogical Faculty , J. E. Purkyne University, Usti nad Labem


From 1,2,3-trichloropropane (TCP), 2,3-dichloroprop-1-ene was obtained by the optimized reaction with dilute aqueous NaOH at 50 oC (yield 88 %) and 2-chloroprop-2-en-1-ol by the reaction with a boiling saturated solution of Na2CO3 or K2CO3 (yield 97-98 %). Reaction times markedly decreased using a phase-transfer catalyst or microwave heating. Prop-2-yn-1-ol was obtained from the 2-chlorprop-2-en-1-ol by dehydrochlorination with a KOH solution (yield 64-66 %). Bis(2-chloroprop-2-en-1-yl) ether, besides 2-chloroprop-2-en-1-ol, was a product of the reaction of TCP with a NaOH solution at 80 - 100 oC.


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