Mesityl chloride, hydrolysis

Mesitoic acid has been prepared by carbonation of mesityl-magnesium bromide 2-4 by hydrolysis of its amide prepared by condensation of mesitylene with carbamyl chloride under the influence of aluminum chloride 6 by oxidation of isodurene with dilute nitric acid 6-7 by distillation of 2,4,6-trimethylmandelic acid (low yield) 8 by dry distillation of 2,4,6-trimethyIphenyl-glyoxylic acid 9 by oxidation of the latter with potassium permanganate 10 and by treating 2,4,6-trimethylphenylglyoxylic acid with concentrated sulfuric acid in the cold11 or with heating.12... 

A Cr(VI) sulfoxide complex has been postulated after interaction of [CrOjtClj] with MejSO (385), but the complex was uncharacterized as it was excessively unstable. It was observed that hydrolysis of the product led to the formation of dimethyl sulfone. The action of hydrogen peroxide on mesityl ferrocencyl sulfide in basic media yields both mesityl ferrocenyl sulfoxide (21%) and the corresponding sulfone (62%) via a reaction similar to the Smiles rearrangement (165). Catalytic air oxidation of sulfoxides by rhodium and iridium complexes has been observed. Rhodium(III) and iridium(III) chlorides are catalyst percursors for this reaction, but ruthenium(III), osmium(III), and palladium(II) chlorides are not (273). The metal complex and sulfoxide are dissolved in hot propan-2-ol/water (9 1) and the solution purged with air to achieve oxidation. The metal is recovered as a noncrystalline, but still catalytically active, material after reaction (272). The most active precursor was [IrHClj(S-Me2SO)3], and it was observed that alkyl sulfoxides oxidize more readily than aryl sulfoxides, while thioethers are not oxidized as complex formation occurs. 

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