A modification of the mechanism of formation of methyl galactosides by the Fischer reaction including a computer simulation

Abstract

The Fischer reaction of d-galactose and methanol, catalyzed by a strongly acidic ion-exchange resin, to form the four methyl galactosides has been run at two temperatures under conditions that allow a computer simulation of the mechanism. The reaction was followed by gas-liquid chromatography of the trimethylsilyl ethers. The data obtained differs appreciably from that described in a previous paper [ J. Org. Chem., 38 (1973) 3272–3277)] owing to an error in peak assignment in that paper. The mechanism previously proposed, however, has required only a slight modification to explain the new data. A possible set of rate constants, equilibrium constants, and apparent activation energies which fit the experimental data have been obtained.