One of the industrial processes for the preparation of phenol, discussed in Section
Chapter 22, Problem 22.34(choose chapter or problem)
One of the industrial processes for the preparation of phenol, discussed in Section 22.6, includes an acid-catalyzed rearrangement of cumene hydroperoxide as a key step. This reaction proceeds by way of an intermediate hemiacetal: C(CH3)2 OOH Cumene hydroperoxide H2SO4 H2O H2O OC(CH3)2 OH Hemiketal OH Phenol CH3CCH3 O Acetone You learned in Section 17.8 of the relationship among hemiketals, ketones, and alcohols; the formation of phenol and acetone is an example of hemiketal hydrolysis. The formation of the hemiketal intermediate is a key step in the synthetic procedure; it is the step in which the aryl oxygen bond is generated. Can you suggest a reasonable mechanism for this step?
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