Sulfuryl chloride → 2-Chloro-5-(hexadecan-2-yl)benzene-1,4-diol

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Reaction Steps

33.5 g (0.1 mol)of 2-sec-hexadecylhydroquinone was dissolved in 300 ml of methylene chloride and to a resulting solution was added dropwise 8.1 ml (0.1 mol) of sulfuryl chloride with stirring at room temperature over a period of 30 minutes. After stirring for 6 hours at room temperature, the reaction mixture was allowed to stand overnight and extracted with ethyl acetate. The extract was washed three times with a 5% aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography (solvent: chloroform) to obtain 27 g of the desired 2-chloro-5-sec-hexadecylhydroquinone as the light from oily product. The structure thereof was confirmed by NMR and mass spectra.

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