PRODUCTION AND PROPERTIES OF 2,3-BUTANEDIOL: XXVII. CRYSTALLINE ESTERS SUITABLE FOR IDENTIFICATION AND ESTIMATION OF THE ISOMERIC 2,3-BUTANEDIOLS

Abstract

The monoacid phthalates, di-p-nitrobenzoates, di-m-nitrobenzoates, di-3,5-dinitrobenzoates, di-p-bromobenzoates, and di-p-methoxybenzoates of levo-, and meso- and dl-2,3-butanediol were prepared to find which derivatives had the best properties for the identification of 2,3-butanediol isomers in a mixture. These are new compounds with the exception of the levo- and dl-monoacid phthalates and the meso-di-p-bromobenzoate. A procedure is given by which the optical isomers present in a 1 gm. sample of 2,3-butanediol can be identified, and the relative amounts of each estimated. They are converted to the di-p-nitrobenzoates, dissolved in chloroform, polarized to determine the concentration of the optically active isomers, and then fractionally crystallized for identification and estimation of relative amounts of the dl- and meso-esters.