Ethyl toluene sulfonate

Fusion of methyl or ethyl toluene- -sulfonates with 4-hydroxy-6-methyl-l,3,3a,7-tetraazaindene (135) gives only one salt, which on treatment with alkali is converted into a N-alkyl-4-oxo derivative. 

From ethyl />-toluene sulfonate and potassium bromide. Rodionov, Bull. soc. chim. (4) 39, 305 (1926). 

A Preparation of 11 -Methoxy-A -Estradiene-3,17-Dione 0.5 g of A -estradiene-11/3-ol-3,17-dione were dissolved at room temperature in 25 cc of methylene chloride containing 2% of methanol and after 5 mg of p-toluene-sulfonic acid were added, the reaction mixture was agitated for several minutes. Then the reaction mixture was poured into ice water, washed with water until the wash waters were neutral, and distilled to dryness under vacuum. The resulting residue was crystallized from ethyl ether to obtain 0.46 g of 11/3-methoxy-A -estradiene-3,17-dione having a MP of 140°C. 

Hydrotropes (LD, DW, HC) Maintain product homogeneity Ability to increase surfactant solubility Color and odor Cumene sulfonate Ethyl alcohol Toluene sulfonates 0-10% 0-10%... 

Vanilla flavour is not only determined and characterised by the vanillin molecule, but also by many more phenolic compounds and vanillin derivatives. Two examples of molecules that recently obtained FEMA-GRAS status are vanillyl ethyl ether and vanillin 2,3-butanediol acetal (Scheme 13.11). Vanillin can be hydrogenated to form vanillyl alcohol, which is also used in vanilla flavours. Vanillyl alcohol can be reacted with ethanol to form vanillyl ethyl ether. Vanillin can also form an acetal with 2,3-butanediol (obtained by fermentation of sugars) catalysed byp-toluene sulfonic acid in toluene. 

One Sanofi synthesis of enantiomerically pure (-i-)-clopidogrel (2) utilized optically pure (R)-(2-chloro-phenyl)-hydroxy-acetic acid (20), a mandelic acid derivative, available from a chiral pool. After formation of methyl ester 21, tosylation of (/ )-21 using toluene sulfonyl chloride led to a-tolenesulfonate ester 22. Subsequently, the Sn2 displacement of 22 with thieno[3,2-c]pyridine (8) then constructed (-i-)-clopidogrel (2). Another Sanofi synthesis of enantiomerically pure (-i-)-clopidogrel (2) took advantage of resolution of racemic a-amino acid 23 to access (S)-23. The methyl ester 24 was prepared by treatment of (S)-23 with thionyl chloride and methanol. Subsequent Sn2 displacement of (2-thienyl)-ethyl para-toluene-sulfonate (25) assembled amine 26. 

Dinitro-ethyl-p-toluene sulfonate 6 E333-E334... 

Aromatic esters and sulfonates (benzyl acetate, ethyl p-toluene-sulfonate) accumulator column 6 46-87 69 7-17 12 d... 

A good source of uncommon bases is tRNA. It provides substrates for studying the effect of base on the rate of hydrolysis. Baev et al. (62) showed that V2-dimethylguanylyl-(3 -5 )-cytidine-3 phosphate (G2m-pCp) was hydrolyzed much slower than the usual GpCp. Venkstern (63) reported that Tp was hydrolyzed very slowly. Naylor et al. (64) found that Cp was hydrolyzed with half the rate of CpU. The same group of workers introduced (64, 65) a chemical block on uridine and pseudo-uridine residues by reacting RNA with l-cyclohexyl-3-(2-morpho-liny]-(4)-ethyl)-carbodiimide metho-p-toluene sulfonate. The modification of the uridine residues completely blocked the action of venom exonuclease and also blocked the action of pancreatic RNase. 

The carbonyl compound (10 mmol) was introduced in the reactor of a Synthe-wave 402 single mode apparatus followed by the acidic catalyst, para-toluene sulfonic acid (PTSA) 10% or montmorillonite clay KSF 1 g (10 mmol) and the reagent (methyl or ethyl orthoformate, 2 equiv.). After irradiation, the product is filtered or washed by a solution of NaHC03 to remove the catalyst and the product is purified by distillation or recrystallization. 

In 1897, it was observed889 that potassium iodide (in hot alcohol or acetone) converts ethyl p-bromobenzenesulfonate to ethyl iodide. Many years later, methyl and ethyl iodides 49 841 and ethyl a-iodopropionate808(b) were prepared in good yield by the action of the same iodide (in boiling water or alcohol) on the corresponding p-toluene-sulfonates. In these examples, the reaction obviously proceeded as an alkyl-oxygen fission, in accordance wi h the following equation ... 

A solution of 3p-hydroxy-5a-pregn-16-ene-ll,20-dione (39.6 g) in dry pyridine (165 ml) was treated with toluene-p-sulfonyl chloride (43.9 g) to give the toluene sulfonate (56.7 g), melting point 147-151°C. A portion (10.7 g) of this material was crystallized from ethyl acetate-petroleum to give the pure 3p-toluene-p-sulfonyloxy-5a-pregn-16-ene-ll,20-dione (9.2 g) as plates, melting point 154°-155°C. 

A solution of 4.9 g (12.8 mmol) of methyl-l-(p-nitrobenzoyl)-5-methoxy-2-methyl-3-indolylacetate in 40 ml of acetic acid containing 400 mg of p-toluene-sulfonic acid is refluxed for 20 hours and then concentrated in vacuum. The gummy residue is extracted with ethyl acetate. The extract is filtered from insoluble material, washed with water and dried over sodium sulfate. Removal of the solvent under reduced pressure affords the desired product as yellow crystals MP 185-186°C. 

To a solution of the catalyst (0.1 mmol), p-toluene sulfonic acid monohydrate (0.1 mmol) and the nitroalkene (0.5 mmol) in DMF (1 mL) was added the ketone (0.25 mmol). The solution was stirred at ambient temperature under reduced pressure, and the residue purified by FC on silica gel. Alternatively, ethyl acetate was added, and the solution washed with water, 1 M HCl, dried (Na2S04), and concentrated to give the crude product which was purified by FC on silica gel. 

Dick (38, 39) has shown that a number of 1-alkylaziridines are converted into the corresponding 1,4-dialkylpiperazines in yields as high as 95%, when treated with hydrohalic acids in acetone or methyl ethyl ketone. Perchloric acid and p-toluene-sulfonic acid resulted in the formation of poly(l-alkylaziridines) rather than piperazines. The major products formed in a water solvent were the polymers with 1,4-dialkylpiperazines being formed in maximum yields of 27% in the case of hydroiodic acid. The mechanism proposed by Dick is, that the piperazine are formed via a dimer in which the halogen atom of the initiating acid has formed a covalent bond with a... 

It should be mentioned at this point that the ease of alkylation of the isotrithiones to isotrithionium salts (251) is not due to any specific stability of the 2-methylmercapto-1,3-dithiolium ion, in which the C=C double bond takes part in the mesomeric system and contributes a pair of it electrons to the aromatic sextet. As was recently shown by Wizinger et aZ.,138 Gompper,157 and Mayer and Schafer158 the dihydroisotrithiones (257) can also be readily alkylated by heating with alkyl halides, dimethyl sulfate, or ethyl p-toluene-sulfonate. Results obtained so far indicate that the reactivity of these dihydroisotrithionium salts towards C, 0, N, and S bases corresponds closely to that of the isotrithionium salts. ... 

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