1,4-Cyclohexanediol, from hydroquinone

Kennedy and Stock reported the first use of Oxone for many common oxidation reactions such as formation of benzoic acid from toluene and of benzaldehyde, of ben-zophenone from diphenylmethane, of fratw-cyclohexanediol from cyclohexene, of acetone from 2-propanol, of hydroquinone from phenol, of s-caprolactone from cyclohexanone, of pyrocatechol from salicylaldehyde, of p-dinitrosobenzene from p-phenylenediamine, of phenylacetic acid from 2-phenethylamine, of dodecylsulfonic acid from dodecyl mercaptan, of diphenyl sulfone from diphenyl sulfide, of triphenylphosphine oxide from triphenylphosphine, of iodoxy benzene from iodobenzene, of benzyl chloride from toluene using NaCl and Oxone and bromination of 2-octene using KBr and Oxone126. Thus, they... 

Zymalkowski and Strippel hydrogenated dihydroxybenzenes with only slight hydrogenolysis over rhodium-platinum oxide in acetic acid at room temperature and 10 MPa H2 and obtained the corresponding cyclohexanediols in 92-96% yields (eq. 11.17).97 The hydrogenations at atmospheric pressure required much longer reaction times, and the yield of cyclohexanediol decreased to 86% with resorcinol. The proportions of cis isomer in the cyclohexanediols obtained at 10 MPa H2 were 81% from catechol, 68% from resorcinol, and 68% from hydroquinone and always greater than those obtained at atmospheric pressure (75,49, and 52%, respectively). 

Hydroquinone is reduced by a nickel-on-kieselguhr catalyst to cis- and /ra is-l,4-cyclohexanediols. Other eyelohexanediols and meth-oxycyclohexanols are formed from dihydric phenols and their monomethyl ethers. /S-Naphthol may be reduced in either ring, depending upon the catalyst and conditions. ... 

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