I was thinking of ways to synthesize 2,2-bis(dihydroxyphenyl) propane and I thought it could be made by a condensation reaction between dihydroxybenzene (catechol) and acetone in strongly acidic conditions.

At first, the catechol would probably form the acetal (even though the former compound could also take part in the reaction). This would then react with acetone, form a cation and this would react with another molecule of the catechol. At last, the diacetal would be hydrolyzed to make the desired compound.

My question is, whether this makes sense. I am especially worried about self-condensation of acetone, which might ruin the reaction.


  • 5
    $\begingroup$ If you replace your diphenol by ordinary phenol, the reaction works perfectly. It is even a usual method for making 2.2-bis(p-hydroxyphenyl)propane, which the starting point for producing epoxy resins. $\endgroup$
    – Maurice
    Feb 26 '20 at 17:23

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!

Condensation product


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