Ethylene Glycol → HCID 11483263, compound

Participants

Reaction Steps

1-(3,5-Dimethoxyphenyl)heptan-1-one (200 mg, 0.80 mmol), ethylene glycol (173 mg, 2.80 mmol) and a catalytic amount of p-toluenesulfonic acid monohydrate were refluxed in toluene (25 mL) overnight in a Dean-Stark apparatus. The reaction mixture was then concentrated and the residue dissolved in chloroform (50 mL) and washed with saturated sodium bicarbonate solution (2×25 mL) then brine (1×25 mL). The organic phase was dried (Na2SO4) and evaporated to give 2-(3,5-dimethoxyphenyl)-2-hexyl-1,3-dioxolane (41) as a light yellow oil (213 mg, 90%). 1H NMR (CDCl3, 300 MHz): δ 0.94, t (6.5 Hz), CH3; 1.31, m, methylene envelope; 1.89, m, CH2; 3.79-3.83, m, 2×OMe, OCH2; 4.04, m, OCH2; 6.46, m, H4′; 6.63, m, H2′,6′. ESI (+ve) MS: m/z 295 (M+H, 62%).

Provenance & Evidence