Ethylene Glycol → 2-(3-Methylthiophen-2-yl)-1,3-dioxolane

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Reaction Steps

To a solution of 3-methylthiophene-2-carbaldehyde (3.53 g, 28.0 mmol) in toluene (75 ml) were added ethylene glycol (31.2 ml, 560 mmol) and a catalytic amount of para toluenesulfonic acid. The mixture was heated under reflux for 17 hr while separating generated water using Dean-Stark trap. The reaction mixture was cooled to room temperature, washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Merck 7734 80 g, ethyl acetate:hexane=1:10) to give 2-(3-methylthiophen-2-yl)-1,3-dioxolane (3.93 g, 23.1 mmol, yield 82.5%) as a pale-yellow oil.

Provenance & Evidence