Vanillin → Catechol

Participants

Reaction Steps

It is known that aromatic aldehydes decarbonylate when heated over hydrogenation catalysts. Of the aromatic aldehydes containing a phenolic group, vanillin is reported to decarbonylate over nickel at 370°-390° C., giving guaiacol and catechol. It is reported (Synthesis, December, 1969, p. 164) that salicylaldehyde in refluxing toluene and in the presence of a stoichiometric amount of chloro-tris(triphenyl phosphine)-rhodium complex yields phenol in 70% yield.

Provenance & Evidence