Abstract
Substituted 2-ethylphenols when heated at or above 550 °C produce substituted benzofurans along with other products. 4-Methyl-, 4-ethyl-, 4,5-dimethyl, 4-fluoro-, 6-fluoro-, 4-chloro-, 6-chloro-, 4,6-dichloro-, and 4-bromo-2-ethylphenols gave the appropriately substituted benzofurans. Substitutent loss was observed in several cases but was most pronounced with the bromo-substituent. Substituent rearrangement with these reactants was absent. Side-chain substitution as in 2-propylphenol gave 2-methylbenzofuran along with some 3-methylbenzofuran. Rearrangements of furan ring substituents were common. 2-Ethylanisole also undergoes the same reaction. 2-Ethylanisole-4- d cyclized to benzofuran-5- d without scrambling. Various catalysts and carrier gases were examined, of which carbonyl sulfide was most selective for benzofuran formation.
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