p-Toluenesulfonic acid → 2-(2-Methoxymethoxyethyl)thiophene

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Reaction Steps

150 g of 2-thiopheneethanol was dissolved in 2,250 mL of dimethoxymethane, and 22.3 g of p-toluenesulfonic acid and 20.3 g of lithium chloride were added thereto. The resulting mixture was refluxed for 5 hours and concentrated by evaporation under reduced pressure. To the residue, 1,000 mL of water and 1,500 mL of n-hexane were added, and the resulting mixture was stirred for 5 minutes. Aqueous layer was discarded, and the organic layer was washed twice with 700 mL portions of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 193 g (yield of 96%) of the title compound as a colorless oil.

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