Resorcinarene - Synthesis

Synthesis

The resorcinarene macrocycle is typically prepared by condensation of resorcinol and an aldehyde in concentrated acid solution. Recrystallization typically gives the desired isomer in quite pure form. However, for certain aldehydes, the reaction conditions lead to significant by-products. Therefore, alternative condensation conditions have been developed, including the use of Lewis acid catalysts.

A green chemistry procedure was recently developed using solvent-free conditions: resorcinol, an aldehyde, and p-toluenesulfonic acid are ground together in a mortar and pestle at low temperature. A paste-like solid forms upon sitting for several minutes, which can be washed with water and crystallized to give the desired resorcinarene.

Under each of these conditions, aromatic aldehydes react much faster, but less stereoselectively than aliphatic aldehydes, and the reaction frequently leads to a mixture of desired and undesired products.

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