Note on the tosylation of diethyl mucate

Abstract

In connection with certain studies on sulfonic esters of sugar derivatives, a sample of diethyl tetra-O-p-tolylsulfonylmucate (p-tolylsulfonyl = "tosyl"; Ts) was desired. Its preparation, by reaction of diethyl mucate (galactarate) with p-toluenesulfonyl chloride in pyridine, was expected to be a simple procedure. However, under all conditions tried, we were unable to isolate any of the compound.6Pittsburgh 13, Pennsylvania

Highly Efficient Chemical Process To Convert Mucic Acid into Adipic Acid and DFT Studies of the Mechanism of the Rhenium‐Catalyzed Deoxydehydration

“…In fact, higher reaction temperature led to lower selectivity, but the reaction was sluggish at lower reaction temperature (90 °C). To understand more about this reaction, the diethylmucate ( 6 ; Scheme ) was prepared according to a reported method16 and was used as the starting material for the DODH reaction. Under the same reaction conditions, full conversion of 6 into 5 (30 %) and 7 (70 %) were achieved at 20 hours (see Figure S1 in the Supporting Information).…”

Highly Efficient Chemical Process To Convert Mucic Acid into Adipic Acid and DFT Studies of the Mechanism of the Rhenium‐Catalyzed Deoxydehydration

“…This outcome could be due to the low solubility of 1 or the interference of carboxylic acid groups. Despite the fact that 6 has much better solubility than 1 in hot alcohols, [16] the reaction of 6 proceeded only slightly faster than that of 1. To understand more about this reaction, the diethylmucate (6; Scheme 1) was prepared according to a reported method [16] and was used as the starting material for the DODH reaction.…”

“…In fact, higher reaction temperature led to lower selectivity, but the reaction was sluggish at lower reaction temperature (90 8C). To understand more about this reaction, the diethylmucate (6; Scheme 1) was prepared according to a reported method [16] and was used as the starting material for the DODH reaction. Under the same reaction conditions, full conversion of 6 into 5 (30 %) and 7 (70 %) were achieved at 20 hours (see Figure S1 in the Supporting Information).…”

“…Apparently, the ester exchange reaction occurred and 65.0 % of the ethyl groups were substituted by 3-pentanol. Despite the fact that 6 has much better solubility than 1 in hot alcohols, [16] the reaction of 6 proceeded only slightly faster than that of 1. This result indicated that 1 was first subject to esterification before undergoing the DODH reaction.…”

Kinetics of thermal polymerization of shellac. V. Turbidimetric and fractionation studies

“…It stops when the potential of the liquid phase equals that of the solid phase. 17 The theories of crystal growth are now discussed. According to the migration theory,18 the incoming unit is not immediately incorporated in the growing phase even if it has arrived on the site by diffusion.…”