To obtain the subject compound by catalytic hydroxylation of nitrobenzene followed by etherification reaction of the formed hydroxyl group with a halogenated olefin from readily available starting substances avoiding the multi-step, long reaction sequence.
A nitrobenzene represented by formula I (R5 and R6 are each H, a halogen) is catalytically hydroxylated in a reaction medium of 5-30wt.% of an aqueous acid solution prepared by using 0.5-10 equivalents of an acid such as sulfuric acid, per equivalent of the compound of formula I, in the presence of a catalyst of a noble metal, for example, platinum to form free aminophenol of formula II. The reaction is carried out at 50-160°C under the pressure of 1-50 bar. Then, the compound of formula II is allowed to react with a halogenated olefin of formula III (R1 is H, a halogen; R2-R4 are each H, a halogen) in the presence of 1-50% of a base and 0.5-30% of water at 0-120°C under the pressure of 0.5-5 bar to give the objective p-haloalkoxyanilin represented by formula IV.
ALBRECHT MALHOLT
GUIDO STEPHAN
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