4-Benzyloxyaniline → Ethylene Oxide

Participants

Reaction Steps

Phenol N-mustard is synthesized by to known procedures with modification. Scheme 4 shows the synthetic route for phenol mustard. Treatment of 4-nitrophenol (20) with benzyl chloride or 4-fluoro-1-nitrobenzene (22) with benzyl alcohol in the presence of base (such as NaOH, KOH, Na2CO3, K2CO3 or organic base) gives compound 21, which is converted into 4-benzyloxyaniline (23) by reduction (Fe/CH3COOH or Pd/C, H2). Treatment of 23 with ethylene oxide affords 4-N,N-bis(2-hydroxyethyl)aminophenyl benzyl ether 24.37

Provenance & Evidence