P-Toluenesulphinic acid

Notes, (a) Commercial p-toluenesulphinic acid sodium salt was dissolved in water and acidified with dilute sulphuric acid. The precipitated sulphinic lacid was filtered off and dried at 20 C/0.1 mmHg. 

Few racemic alkyl p-tolyl sulphoxides were prepared in rather low yields (16—40%) by the reaction of Grignard reagents with mixed anhydrides 108, 109 and compound HO formed in situ from p-toluenesulphinic acid and 3-phthalimidoxy-l,2-benzoisothiazole 1, 1-dioxide167 (equation 59). The mixed anhydrides 109 or 110 when reacted with cyclopen-tene and cyclohexene enamines 111 gave the corresponding a-ketocycloalkyl sulphoxides 112 in low yields (10-41%) along with small amounts of several by-products such as disulphides and thiosulphonates167 (equation 60). 

To prepare the free sulphinic acid, dissolve some of the sodium salt in cold water and cautiously acidify with hydrochloric acid avoid an excess of mineral acid since it dissolves the sulphinic acid to a certain extent. The resulting p-toluenesulphinic acid is difflcult to dry without partial conversion into the sulphonio acid and thiolsulphonic ester... 

Thoria catalyst, 735 Tischenko reactions, 318 Tollen s ammoniacal silver nitrate reagent, 330, 1061, 1074 p-Tolualdehyde, 689, 697 o-Toluamide, 798 Toluene, 510, 516, 615 purification of, 173, 174 separation from benzene, 231 p-Toluenesulphinic acid, 821, 826 o-Toluenesulphonamide, 821, 824 p-Toluenesulphonamide, 820, 823 p-Toluenesulphonates, 422, 437, 650, 684 ... 

Reaction of enamines with alkyl / -toluenethiosulphonates (p-CH3C6H4S02SC6H13) gives a-alkylmercapto ketones208, and reaction with / -toluenesulphinic acid in the... 

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