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

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.

1. temperatureThe resulting mixture was refluxed for 5 hours
2. concentrationconcentrated by evaporation under reduced pressure
3. additionTo the residue, 1,000 mL of water and 1,500 mL of n-hexane were added
4. washthe organic layer was washed twice with 700 mL portions of water
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-7e60ee98ad784f5ca28f250842bd9e95

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07449580B2