Toluene → 2-[2-(3-Methoxyphenoxy)phenyl]-1,3-dioxolane

Participants

Reaction Conditions

Reaction Steps

Potassium hydroxide pellets (35.2 g; 0.63 mol) were dissolved in water (50 ml) and 3-methoxyphenol (78 g; 0.63 mol) was added together with toluene (250 ml). The mixture was heated to and maintained at reflux temperature until water ceased to distil over (a total of 65 ml of water was collected). The mixture was cooled to 80° C. and 2-(2-bromophenyl)-1,3,-dioxolane (120 g; 0.524 mol), DMF (200 ml) and cuprous chloride (0.2 g) were added. The mixture was slowly heated to 150°-155° C. and toluene was distilled off. The mixture was maintained at 150°-155° C. for 6 hours then cooled to 25° C. and water (500 ml) was added. The mixture was filtered and the residue was washed with ether (200 ml). The filtrate was extracted with ether (3×150 ml). The combined ether extracts were washed with 2N sodium hydroxide solution (2× 150 ml), water (4×150 ml) and saturated brine (1×200 ml). After drying and filtration the ether solution on evaporation gave 2-[2-(3-methoxyphenoxy)phenyl]-1,3-dioxolane (124.1 g, 87.1% yield) as an oil.

Provenance & Evidence