4-Nitrophenol → 2-((4-Nitrophenoxy)methyl)oxirane

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-nitrophenol (0.6 mole, 82.3 grams), epichlorohydrin (1.8 mole, 167 g.) and piperidene (3 ml.) is stirred at 100° C. for 17 hours. The solution is evaporated and to the residue is added sodium hydroxide (2 mole) in 500 ml. of water. After 24 hours of stirring, the solution is extracted with chloroform. After washing with dilute sodium hydroxide, the dried chloroform solution is evaporated yielding 3-(4-nitrophenyloxy)-1,2-epoxypropane. A solution of the epoxide (1.0 g.) in 50% aqueous acetic acid (15 ml.) is heated at 90° C. for five hours and then evaporated and chromatographed on silica acid plates (chloroform-methanol 9:1). The band with an Rf of about 0.5 is eluted and crystallized from chloroform and ethyl acetate to yield 1,2-dihydroxy-3-(4-nitrophenyloxy)-propane.

Provenance & Evidence