Superacid Catalysed Hydroxyalkylation of Aromatics with Ethyl Trifluoropyruvate

(A New Route to Mosher’s Acid Analogues)

A recent paper by G.K. Surya Prakash and George Olah describes the reaction of ethyl trifluoropyruvate with a variety of activated aromatic and heteroaromatic substrates (such as using trifluoromethanesulphonic acid or gallium trifluoromethanesulphonate as catalyst.

Yields are generally excellent (mainly >90% ), but occasionally lower (84% with p-xylene, 40% with N-methylpyrrole for example) and regioselectivity is 100% for most substrates with the exception of toluene and anisole where the regioselectivity is 94% and 92% respectively.   ( Synlett , 2003 (4), 527-531).