Epichlorohydrin → Methyl 3-{4-[(oxiran-2-yl)methoxy]phenyl}propanoate

Participants

Reaction Steps

A mixture of 228 gm (1.27 mole) of methyl 3-(4-hydroxyphenyl)propionate, 263 gm (1.90 mole) of K2CO3 and 298 mL (3.80 mole) of epichlorohydrin in 2 liters of acetone was stirred and heated to reflux for 20 hours. The reaction medium was then filtered and evaporated under reduced pressure. The resulting oil was taken up in 1 liter of toluene andwashed consecutively with 500 mL water, 2×500 mL 1N NaOH and 2×500 mL water. The toluene phase was then dried over MgSO4 andevaporated under reduced pressure to provide a clear oil which was further purified by vacuum distillation. The final yield of purified oil was 131.2gm (44%): bp 156° (p=0.4 mm Hg). The NMR and IR spectra of the product were consistent with the assigned structure and the elemental analysis was consistent with the formula C13H16O4.

Provenance & Evidence