Ethylene Glycol → HCID 22615139, compound

Participants

Reaction Steps

A solution of 5.00 g (30.00 mmol) 2-fluoro-4-methoxyacetophenone, 1.11 ml (33.00 mmol) ethylene glycol and 0.28 g (1.49 mmol) p-toluene sulfonic acid hydrate in 50 ml toluene was refluxed in a Dean-Stark apparatus for 2.5 days. After 0.5 and 1.5 days additional 1.11 ml (33.00 mmol) ethylene glycol and 0.28 g (1.49 mmol) p-toluene sulfonic acid hydrate were added. After cooling, the reaction was diluted in ether and washed with aqueous saturated NaHCO3 (two times) and aqueous 10% NaCl solution. The water phases were extracted with ether, the organic phase was dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography (SiO2; n-heptane/AcOEt=95:5) to give 4.90 g of the title compound as brown liquid (with ca 10% of starting material, seen in 1H-NMR).

Provenance & Evidence