Nitrogen → 2-[(4-Allyl-2-methoxyphenoxy)methyl]oxirane

Participants

Reaction Steps

A 2,000 mL, 3-necked, round-bottom flask was equipped with a mechanical stirrer, a 250 mL pressure equalizing addition funnel and a reflux condenser. The addition funnel served as the N2 inlet and the reflux condenser served as the N2 outlet. The flask was purged with a vigorous stream of N2 for 10 min. prior to its use. The flask was charged with epichlorohydrin (740 g, 8.0 mol) and eugenol (328 g, 2.0 mol). These were heated to ca. 80° using a heating mantle while stirring at a moderate rate (ca. 500 rpm). The 50% NaOH (168 g, 2.0 mol) was placed in the addition funnel and was added dropwise to the reaction flask over a 3 hour period. The mixture was allowed to cool and was filtered through a Buchner funnel. The epichlorohydrin was removed by rotary evaporation. The residue was taken up in CH2Cl2 (800 mL) and was washed with 10% NaOH (100 mL) brine and dried (Na2SO4). The crude product was vacuum distilled through a 10 cm Vigreux column to yield 4-allyl-2-methoxyphenyl glycidyl ether, i.e., ##STR22##

Provenance & Evidence