The pinacol rearrangement is essentially a dehydration reaction of an alcohol, specifically a diol. The following is an example of a pinacol rearrangement in which the (R,R)-diol (TBDMS is tert-butyldimethylsilyl) was allowed to react with 2,2 dimethylpropane (2,2-DMP) in the presence of boron trifluoride etherate at room temperature. This particular reaction was done in order to attain the acetone derivative.

Interestingly, instead of retaining its chirality, the product of the pinacol arrangement actually resulted in a racemic mixture. Subsequent derivatives of this product eventually yield benzophenone (hydroxyphenstatin), which, biologically, is a potent antitumor and antimitotic agent. Accordingly, hydroxyphenstatin has also been proven to inhibit tubulin assembly.

Phenol is more important than most people realize. It can be found in many consumer products including aspirin, head lights, gas tanks, billiard balls, nylon, wintergreen gums, Pepto Bismol, deodorant and more. A side product in the manufacture of phenol is acetone which is also used in the private sector in plastics, solvents, and more.

The high-yield manufacture of phenol uses the concepts of peroxidation and cleavage. Cumene (i-propyl benzene) is oxidized by exposure to air to temporarily produce cumene hydroperoxide. The cumene hydroperoxide is simply cleaved at the top of the benzene ring using an acidic catalyst to produce the two usable products of phenol and acetone. The catalyst is extracted and the phenol/acetone mixture is fractionated and purified. Under optimal conditions, 1.31 tons of i-propyl benzene (cumene) will produce 1 ton of phenol and 0.615 tons of acetone. The end-product phenol purity is at 99.99 wt % with total impurities of only 60 ppm. This process is termed the Hock process after being discovered by Hock and Lang in 1944. This process was ideal since both products were useful and relatively pure. Modern demand, however, for phenol is increasing at a higher rate than acetone. This means that the future may classify acetone as a partial waste product. More information on the Hock Process of manufacturing Phenol can be found here which expands on the Benzene-Free Synthesis of Phenol or here which discusses Selective decomposition of cumene hydroperoxide into phenol and acetone by a novel cesium substituted heteropolyacid on clay.