AQUEOUS HIGH-TEMPERATURE CHEMISTRY OF CARBOCYCLES AND HETEROCYCLES .10. AQUATHERMOLYSIS OF ACYCLIC AND CYCLIC PHENOL ETHERS IN THE PRESENCE OF SODIUM BISULFITE OR PHOSPHORIC-ACID

On aquathermolysis in a sulfite/bisulfite mixture, anisole and n-butyl phenyl ether show 27% and 19% cleavage conversion, respectively, with phenol as the only product. In 10% aqueous phosphoric acid, in addition to phenol, small amounts of alkylated products were also observed. When phenol was reacted with methanol or butanol in 10% phosphoric acid, the same slates of products were obtained as had been obtained from the corresponding ethers. As negligible conversions were seen in cyclohexane, acid-catalyzed ionic mechanisms are proposed. 2,3-Dihydrobenzofuran also gave phenol as the major product with some alkylphenols and dimers. Diphenyl ether showed no conversion under the conditions employed. © 1990, American Chemical Society. All rights reserved.