Pyrogallol → Bendiocarb phenol

Participants

Reaction Steps

A stirred mixture of 10.0 grams (0.079 mole) of benzene-1,2,3-triol, 20 mL (0.163 mole) of 2,2-dimethoxypropane and 1.0 gram (catalyst) of Amberlite® IR-120 (plus) ion exchange resin in 50 mL of toluene was warmed to 100° C., where it was maintained during an 18 hour period. After this time the reaction mixture was concentrated under reduced pressure to a residual solid. The solid was triturated with three 50 mL portions of methylene chloride. The combined organic extracts were concentrated under reduced pressure to a residual solid, which was then dissolved in methylene chloride and subjected to column chromatography on silical gel. Elution was accomplished with 1:4 ethyl acetate:hexane. A second column chromatography as described above was needed to purify the solid. In each chromatography, the appropriate fractions were combined and concentrated under reduced pressure, ultimately yielding 5.3 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence