Synthesis of half esters

Abstract

A method for hydrolyzing an ester is provided. In accordance with the method, a compound A is provided which has first and second ester moieties. The compound is reacted in a liquid medium with a base having the formula M a X b , such that the first ester moiety is converted to a carboxyl moiety and the second ester moiety remains, wherein the ratio [X k− ]:[A] in the liquid medium is no greater than 1.6, and wherein k>0.

1 - 55 . (canceled) 
     
     
         56 . A method for hydrolyzing an ester, comprising:
 providing a first symmetric compound having first and second ester moieties;   reacting the compound with a base in an aqueous medium to form a first product such that the ratio of the number of molar equivalents of base to the number of molar equivalents of the first compound is greater than 3; and   quenching the reaction through acidification to form a second product such that the total reaction time is no greater than 90 minutes.   
     
     
         57 . The method of  claim 56 , the ratio of the number of molar equivalents of base to the number of molar equivalents of the first compound is greater than 5. 
     
     
         58 . The method of  claim 56 , the ratio of the number of molar equivalents of base to the number of molar equivalents of the first compound is greater than 7. 
     
     
         59 . The method of  claim 56 , the ratio of the number of molar equivalents of base to the number of molar equivalents of the first compound is greater than 10. 
     
     
         60 . The method of  claim 56 , wherein the first compound is a cyclic compound. 
     
     
         61 . The method of  claim 56 , wherein the first compound is a bicyclic compound. 
     
     
         62 . The method of  claim 61 , wherein the first compound is a bicyclic diene. 
     
     
         63 . The method of  claim 56 , wherein the first compound is a cyclic diester. 
     
     
         64 . The method of  claim 56 , wherein the total reaction time is no greater than 60 minutes. 
     
     
         65 . The method of  claim 56 , wherein the total reaction time is within the range of about 10 minutes to about 60 minutes. 
     
     
         66 . The method of  claim 56 , wherein the total reaction time is within the range of about 20 minutes to about 60 minutes. 
     
     
         67 . The method of  claim 56 , wherein the reaction produces a second compound, and wherein the second compound is a half ester. 
     
     
         68 . The method of  claim 56 , wherein the first and second ester moieties are bonded to first and second adjacent carbon atoms, and wherein said first and second carbon atoms are bonded to each other by a double bond. 
     
     
         69 . The method of  claim 68 , wherein said first and second carbon atoms are part of a ring. 
     
     
         70 . The method of  claim 69 , wherein said ring is part of a bicyclic structure. 
     
     
         71 . The method of  claim 56 , wherein the first compound is dimethyl bicyclo[2.2.1]hept-2,5-diene-2,3-dicarboxylate. 
     
     
         72 . The method of  claim 56 , wherein the second product is a half ester. 
     
     
         73 . The method of  claim 56 , wherein the base has the formula M a X b , wherein the first ester moiety is converted, through the reacting and quenching steps, to a carboxyl moiety, and wherein the second ester moiety is still an ester moiety after the reacting and quenching steps. 
     
     
         74 . The method of  claim 56 , wherein the base is selected from the group consisting of LiOH, NaOH, KOH and CsOH. 
     
     
         75 . The method of  claim 56 , wherein the first compound is reacted with the base at a temperature T, and wherein −15° C.<T<15° C.