Methyl p-toluenesulphonate

Metho-p-toluenesulphonate. Methyl p-toluenesulphonate combines with many tertiary amines to yield crystalline deiivates ... 

The benzyl chloride quaternary salts RR R"NC3HsCH2 +Cl are prepared similarly 3 g. of redistilled benzyl chloride replaces the methyl p-toluenesulphonate. 

Methyl p-toluenesulphonate. This, and other alkyl esters, may be prepared in a somewhat similar manner to the n-butyl ester with good results. Use 500 g. (632 ml.) of methyl alcohol contained in a 1 litre three-necked or bolt-head flask. Add 500 g. of powdered pure p-toluene-sulphonyl chloride with mechanical stirring. Add from a separatory funnel 420 g. of 25 per cent, sodium hydroxide solution drop by drop maintain the temperature of the mixture at 23-27°. When all the alkali has been introduced, test the mixture with litmus if it is not alkaline, add more alkali until the mixture is neutral. Allow to stand for several hours the lower layer is the eater and the upper one consists of alcohol. Separate the ester, wash it with water, then with 4 per cent, sodium carbonate solution and finally with water. Dry over a little anhydrous magnesium sulphate, and distil under reduced pressure. Collect the methyl p-toluenesulphonate at 161°/10 mm. this solidifies on cooling and melts at 28°. The yield is 440 g. 

Kaplan and Thornton (1967) determined secondary kinetic isotope effects in two 8 2 displacement reactions, one of which involved quatemi-zation of N,N-dimethylaniline and N,N-dimethyl-eig-aniline with methyl p-toluenesulphonate (CHgOTs). The reactions were carried out in... 

Dissolve 2-3 g. of methyl p-toluenesulphonate in 10 ml. of dry benzene, add 1 g. of the amine, and boil the mixture for 20-30 minutes. Cool, and filter the precipitated quaternary salt. Recrystallise by dissolving the solid in the minimum volume of boiling ethyl alcohol and then adding ethyl acetate until crystallisation commences. Filter the cold mixture, dry rapidly on a porous plate, and determine the m.p. immediately. 

Methyl -propyl ketone, 340 Methyl pyridines, purification of, 177-179 N-Methylpyrrole, 837, 838 Methyl red, 621, 625 sodium salt of, 626 Methyl salicylate, 780,782 Methyl sulphite, 304 2-Methylthiophene, 836 Methyl p-toluenesulphonate, 825 Methylurea, 968, 969 Methylene bromide, 300 Methylene chloride, purification of, 176 3 4-Methylenedioxycinnamic acid, 711, 719... 

Saegusa has investigated the cationic homopolymerisation of the six cyclic imino ethers shown below using methyl iodide and methyl p-toluenesulphonate as initiators. 

With methyl p-toluenesulphonate all polymerisations proceed via ionic intermediates (oxazolinium or oxazinium ions), initiation and propagation being formulated as follows e.g. ... 

In a study of the reactions of methyl p-toluenesulphonate Swain and Morgan determined the ester at 261 nm294. Katritzky and collaborators295 determined sulphonate (and sulphate) esters by extraction into CC14 and measuring in the IR the intensity of the asymmetric S02 stretching mode. 

Solubilization.—Mukherjee has provided a general review of micellar aggregation and solubilization and discussed the microenvironments of benzene and naphthalene in Triton X-100 micelles in terms of a two-state model involving competition of core and surface solubilization. The partition coefficients of p-nitrophenylacetate and methyl p-toluenesulphonate between water and cetyltrimethylammonium bromide micelle have been measured using dialysis by an artificial kidney." Since monomeric surfactant may be transported across the regenerated cellulose membrane, such experiments require careful attention to detail and caution in their interpretation. In the present case, K values obtained accord well with the literature. 

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