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Michael Tam

Condensation reaction between catechol and acetone

Declan Hiam  Follow

Baker (J. Chem. Soc., 1678 (1934)) describes the condensation of catechol with acetone and it went down another path. Indeed the acetone self-condensation interferes with your reaction plan: acetone self-condensation eventually leads to phorone, which condensed with two molecules of catechol to form "5:6:5':6'-tetrahydroxy-3:3:3':3'-tetramethylbis-1:1'-spirohydrindene".

The author gives a very good explanation and analysis of multiple derivatives of this interesting compound. Even without mass spectrometry or NMR results, I completely believe the structural interpretation. Top notch science!

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