McMurry coupling of MOM protected 4-hydroxybenzaldehyde and 3,5-dihydroxybenzaldehyde was investigated. In an effort to find a greener synthetic route, methods of activating inexpensive titanium metal powder were attempted. Neither treatment of titanium powder with dilute acid followed by drying nor reaction with dibromobutane produced titanium that was active in the McMurry reaction. Finally McMurry coupling with titanium metal produced by in situ reduction of TiCl4 was attempted. A shorter and greener approach to the synthesis of resveratrol could result in the more efficient production resveratrol and analogs.

Attempted synthesis of resveratrol by McMurry reaction

251st National Meeting (2016)

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