2,4-Dichlorophenol → 2,6-Bis(3,5-dichloro-2-hydroxybenzyl)-4-fluorophenol

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Reaction Steps

4-fluoro-2,6-bis(hydroxymethyl)phenol (2.0 g) was dissolved in glacial acetic acid (20 ml) and added slowly to 2,4-dichlorophenol (3.8 g) in concentrated H2SO4 at 60°-70°. The mixture was held at 65°-70° for 1 hr, cooled, acetic acid (20 ml) was added to dissolve the solids and the solution was poured into ice-water. The solid precipitate was purified by column chromatography over silica gel using hexane-ethyl acetate as eluent. The title compound was obtained in yield of 1.3 g, mp 168°.

Provenance & Evidence