Epichlorohydrin → [(2-Iodo-5-methoxyphenoxy)methyl]oxirane

Participants

Reaction Conditions

Reaction Steps

A 5.0 g (0.02 mole) sample of 2-iodo-5-methoxyphenol was added in portions to a suspension of 1.01 g (0.021 mole) of 50% sodium hydride (from which the oil had been removed by washing with hexane) in 40 ml of dry DMF. The resulting solution was cooled to 5° C. and 9.14 g (0.099 mole) of epichlorohydrin was added. The mixture was heated at 60° C. for 15 minutes. The mixture was cooled and filtered through diatomaceous earth. The solvent was evaporated in vacuo from the filtrate. The residue was taken up in ether, the ether washed with water and brine, dried (MgSO4) and the solvent evaporated in vacuo to give 5.72 g (93% yield) of [(2-iodo-5-methoxyphenoxy)methyl]oxirane as a brown oil.

Provenance & Evidence