Hydrochloric Acid → p-(Octylthiomethyl)benzyl chloride

참여 물질

반응 단계

1.83 g (19 mmol) of sodium t-butoxide and 2.78 g (19 mmol) of octanethiol were stirred into 40 g of methanol at room temperature. After 30 minutes, the clear solution was added in one portion to 6.68 g (19 mmol) of the p-xylylenebis(tetrahydrothiophenium chloride) obtained in accordance with Example 1, in 100 g of methanol. After one hour, the mixture was neutralized using 1N hydrochloric acid, and all the volatile components were removed under reduced pressure. The crude product was taken up in 200 ml of chloroform, the undissolved constituents were filtered off, and the filtrate was evaporated under reduced pressure. The oil was mixed with twice the volume of octane, and distilled off under reduced pressure together with tetrahydrothiophene. This sequence was repeated three times with octane, finally giving 5.31 g, consisting of 90% of product, 5% of starting material and 5% of p-bis(octylthiomethyl)benzene. This reaction was carried out at various temperatures and the product distribution analyzed by 1H-NMR spectroscopy (all data in mol-%).

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