Sodium periodate → 6-Benzenesulfinyl-hexa-2,4-dienoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-phenylsulfanyl-hexa-2,4-dienoic acid methyl ester (0.336 g, 1.43 mmol) in methanol (17 mL) was added dropwise at 0° C. a solution of sodium metaperiodate (0.37 g, 1.72 mmol) in distilled water (6 mL). The mixture was allowed to warm to 20° C. and then heated at reflux for 5 hours. The solution was concentrated under reduced pressure to give an oil that was dissolved in ethyl acetate (20 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (10 mL), distilled water (10 mL) and then brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an oil that was purified by flash chromatography (1:2 to 1:1 to 2:1 ethyl acetate:60-80 ° C. petroleum ether). The resulting powder was recrystallised from diethyl ether to give the title compound (0.29 g, 81%) as a white solid, mp 82-84° C.

Provenance & Evidence