Sodium p-toluenesulfonate

Sodium p-toluenesulfonate [657-84-1] M 194.2, pK -1.34 (for -SOs"). Dissolved in distilled water, filtered to remove insoluble impurities and evaporated to dryness. Then crystd from MeOH or EtOH, and dried at 110°. Its solubility in EtOH is not high (maximum 2.5%) so that Soxhlet extraction with EtOH may be preferable. Sodium p-toluenesulfonate has also been crystd from Et20 and dried under vacuum at 50°. 

Polar organic solvents with electrolytes such as sodium p-toluenesulfonate are compatible with capillary electrophoresis. Background electrolyte need not be an aqueous solution. [P. B. Wright, A. S. Lister, and J. G. Dorsey, Behavior and Use of Nonaqueous Media Without Supporting Electrolyte in Capillary Electrophoresis and Capillary Electrochromatography, Anal. Chem. 1997, 69, 3251 I. E. Valko, H. Siren, and M.-L. Riekkola, Capillary Electrophoresis in Nonaqueous Media An Overview, LCGC 1997, 15, 560.]... 

Prior to 1932, a year of some significance in this field (see p. 191), the reaction was, for example, applied to the preparation of methyl 2,3,4-tri-0-acetyl-6-deoxy-6-iodo-a-D-glucoside348 (25 hours at 130°), 2,3,4,2, -3, 4 -hexa-0-acetyl-6,6 -dideoxy-6,6 -diiodo-trehalose347 (24 hours at 130° 89% yield), and methyl 2,3,4,2, 3 -penta-0-acetyl-6,6 -dideoxy-6,6,diiodo-/3-cellobioside348 (60 hours at 100° 94% yield of product 100% yield of sodium p-toluenesulfonate). Such products are valuable in the preparation of other co-derivatives, e.g., co-deoxy sugars (see p. 157). 

One sulfonylated aldonic-acid derivative of this type has been tested, viz., methyl 2,4 5,6-di-0-methylene-3-0-tosyl-n-gluconate. On treatment418 with sodium iodide-acetone at 100° it gave free iodine plus sodium p-toluenesulfonate (50%, 2 hours 57%, 4 hours). If heated with sodium iodide-acetic anhydride under reflux for 2 hours, a 98% yield of sodium p-toluenesulfonate resulted. What contribution the carbomethoxy group makes is, as yet, unknown but there is reason to believe181 that it may be considerable. 

Treatment of the monoethylidene-D-mannitol with lead tetraacetate or periodate resulted in the consumption of two molecular equivalents of oxidant with the concomitant production of one mole of formaldehyde, one mole of formic acid and a monoethylidene-D-erythrose, the latter being identified by its conversion into the known crystalline D-erythrosazone.118 This evidence limited the choice of structure for the mannitol acetal to the 1,3- and 2,3-compound (4,6- and 4,5- are the respective identical structures). Two additional facts eliminated the latter alternative, first, the tetratosyl ester gave only one mole of sodium p-toluenesulfonate when heated with sodium iodide in acetone, and secondly, the same monoethylidene-D-mannitol was obtained from the above 1,3,4,6-diethylidene-D-mannitol by acidic hydrolysis.118 For these reasons Bourne, Bruce and Wiggins118 assigned to the mono-, di- and tri-ethylidene-D-mannitols, respectively, the 1,3-, 1,3 4,6- and 1,3 2,5 4,6- structures. 

The electrostatic model for the micellar effect on the hydrolysis of phosphate monoesters is also consistent with the results of inhibition studies (Bunton et al., 1968, 1970). The CTAB catalyzed hydrolysis of the dinitrophenyl phosphate dianions was found to be inhibited by low concentrations of a number of salts (Fig. 9). Simple electrolytes such as sodium chloride, sodium phosphate, and disodium tetraborate had little effect on the micellar catalysis, but salts with bulky organic anions such as sodium p-toluenesulfonate and sodium salts of aryl carboxylic and phosphoric acids dramatically inhibited the micelle catalysis by CTAB. From equation 14 and Fig. 10, the inhibitor constants, K, were calculated (Bunton et al., 1968) and are given in Table 9. The linearity of the plots in Fig. 10 justifies the assumption that the inhibition is competitive and that incorporation of an inhibitor molecule in a micelle prevents incorporation of the substrate (see Section III). Comparison of the value of for phenyl phosphate and the values of K for 2,4-and 2,6-dinitrophenyl phosphates suggests that nitro groups assist the... 

Fig. 3 Dependence of k on sodium p-toluenesulfonate, on mobile-phase concentration of 1-hexanesulfonate. Conditions as in Fig. 1. Experimental data were fitted by Eq. 8. (From Ref [18]. Courtesy of Marcel Dekker, Inc.)...

Chloro-9-phenyl-8-azapurine, stirred with sodium p-toluenesulfonate in dimethylformamide (room temp, 12 min), gave a 41% yield of9-phenyl-6-p-toluenesulfonyl-8-azapurine. The new substituent was shown to be only moderately useful for metatheses. -... 

Reaction with tosylates. The tosylates of primary alcohols react readily with a 10% solution of sodium iodide in acetone to give the corresponding iodides. Thus, as measured by the rate of separation of sodium p-toluenesulfonate, the reactions... 

Electrochemical polymerization of pyrrole-dg doped with sodium p-toluenesulfonate-ds-... 

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