Esters of sulphonic acids

The preparation of the phenacyl-, />-bromophenacyl or />-nitrobenzyl esters of sulphonic acids is usually unsatisfactory. 

The alkyl esters of sulphonic acids exhibit properties similar to those of the alkyl sulphates, and are hydrolysed, by boiling with aqueous alkalis, to the alcohols and sulphonates. Thus with ethyl p-toluenesulphonate ... 

Aryl esters of sulphonic acids (X = —SOaR Section III). 

Also this compound on oxidation yields a true ester of sulphonic acid CeHfi—SO2—OC2H5... 

Thiourea, substituted thioureas, thioamides Sulphonyl halides N-Halosulphonanudes Aldehyde and ketone bisulphite compounds Thiols TJuo-ethers THo-adds Esters of sulphonic acids... 

Additional esters of />-nitro- and 3,5-dinitrobenzoic acids will be found in Tables 6 and 10. Esters of sulphonic acids are dealt with on page 106. 

S. Patai and Z. Rappoport, eds.. The Chemistry of Sulphonic Acids, Esters and Their Derivatives, John Wiley Sons, Ltd., Chichester, U.K., 1991. 

Combined Erythrina Alkaloids. The sources of the liberated alkaloids (see above) are now known to be, at least in two cases, the sulphur-containing alkaloids erysothiopine and erysothiovine, which are esters of sulphoacetic acid, HOOC. CHj. SOj. OH, identified as the aniline salt, m.p. 187-9° with erj sopine and erysovine respectively. The sources of erysodine and erysonine have not yet been isolated. These combined alkaloids arc believed to be sulphonic esters, of the type HO. OC. CHj. SOj. 0. R, where R is the alkaloidal residue. ... 

The chemistry of sulphonic acids, esters and their derivatives The chemistry of alkanes and cycloalkanes Supplement S The chemistry of sulphur-containing functional groups The chemistry of organic arsenic, antimony and bismuth compounds The chemistry of enamines (2 parts)... 

N-Benzylamides are recommended when the corresponding acid is liquid and/or water-soluble so that it cannot itself serve as a derivative. The benzyl-amides derived from the simple fatty acids or their esters are not altogether satisfactory since they are often low melting those derived from most hydroxy acids and from polybasic acids or their esters are formed in good yield and are easily purified. The esters of aromatic acids yield satisfactory derivatives but the method must compete with the equally simple process of hydrolysis and precipitation of the free acid, an obvious derivative when the acid is a solid. The procedure fails with esters of keto acids, sulphonic acids and inorganic acids and some halogenated aliphatic esters. 

Liebman JF (1991) Thermochemistry of sulphonic acids and their derivatives. In Patai S, Rappoport Z (eds) The chemistry of the sulphonic acids, esters and their derivatives. Wiley, Chichester, p 283... 

Sulphonic acids are usually esterified with diazomethane [121] by methods analogous to those used for the preparation of esters of carboxylic acids (see p. 54). If the reaction starts from the salts, it is necessary to convert them into acids either by direct acidification or with the aid of a cation-exchange resin in the H+ form. 

Baker and Boyce [122] determined isomers of toluenesulphonic acid as ethyl esters prepared by the reaction with triethyl orthoformate. About 0.1 ml of sulphonic acid was added to a known amount of toluene (12 ml) and the water produced was removed by azeotropic distillation with about 5 ml of toluene. o-Terphenyl (0.05 g in 3 ml of toluene) was added as an internal standard, followed by a 20-fold excess of triethyl orthoformate, and the solution was refluxed for 15 min. After this period the reaction proceeds quantitatively and the reaction mixture can be injected directly into the chromatograph. The separation was carried out on 3% of OV-101. 

SYNS EMS ENT 26,396 ETHYL ESTER of METHANESULFONIC ACID ETHYL ESTER of METHYLSL LFONIC ACID ETHYL ESTER of METHYLSULPHONICACID ETHYL METHANE-SULPHONATE ETHYL METHANSULFONATE ETHYL METHANSULPHONATE HALF-MYLERAN METHYNESULPHONIC ACID ETHYL ESTER METHYLSULFONIC ACID, ETHYL ESTER NSC-26805 RCRA I tYISTE NUMBER U119... 

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