THE SYNTHESIS OF 4-PHENOXYCATECHOL AND 2-PHENOXYHYDROQUINONE¹

Abstract

As a part of a study of the developing action of certain substituted catechols and hydroquinones, it was necessary to prepare 4-phenoxycatechol (III) and 2-phenoxyhydroquinone (X). The methods used to prepare these compounds are described here.f The synthesis of 4-phenoxycatechol was achieved by the following sequence of reactions: Veratrol was iodinated in carbon tetrachloride solution in the presence of a molar equivalent of silver trifluoroacetate to 4-iodoveratrol (I) in a 1326 solidified on cooling, m.p. 44-45°. Anal. Calc'd for CuHuOs: C, 73.0; H, 6.1.Found: C, 72.8; H, 6.3. 2-Phenoxyhydroquinone (X). A mixture of 28 g. of 2,5-dimethoxydiphenyl ether and 200 g. (1.4 moles) of anhydrous aluminum chloride in 100 ml. of benzene was heated under reflux on a steam-bath for two hours and then poured into ice and hydrochloric acid. The gray solid (20 g. 88%) was recrystallized from dilute acetic acid, m.p. 155°. When the method described for preparing 4-phenoxycatechol was applied to 2-phenoxyhydroquinone dimethyl ether, an 85% yield of the demethylated product was obtained. SUMMARYThe syntheses of 4-phenoxycatechol and 2-phenoxyhydroquinone are described. A method of iodination is given that should have wide application. A new demethylation procedure is reported.

Rigid-rod polyquinolines with extended aryl ether pendent groups: an approach to solubility enhancement

“…Sci., Part A-2 1970, 8, 541. (11) "Handbook of Chemistry and Physics", 58th ed. ; CRC Press: Boca Raton, FL, 1977.…”

“…4-(4-Phenoxyphenoxy)benzyl Alcohol (11). A solution of 16.0 g (50.0 mmol) of methyl 4-(4-phenoxyphenoxy)benzoate (10) in 250 mL of dry ether/tetrahydrofuran, 3:2, was added dropwise over 2 h to a stirred suspension of 1.04 g (27.5 mmol) of lithium aluminum hydride in 50 mL of dry ether at room temperature.…”