β-[3-Iodo-4-(4'-hydroxyphenoxy)phenyl]propionic Acid and Iodinated Derivatives¹

Abstract

may 1961 ß-[3-IODO-4-(4 '-hydroxyphenoxy) phenyl ]propionic acid 1413 (20%), m.p. 158-159°. When mixed with the quinaldoin N,N '-dioxide obtained in the benzoin condensation, no depression in melting point was obtained.A mixture of 0.1 g. of the quinaldoin, 20 ml. of pyridine and 5 ml. of water was allowed to stand for 10 days under an atmosphere of nitrogen. At the end of the period the dark solid which had formed was separated and washed with methanol and ether. The dry product, 0.015 g. (15%), when crystallized from pyridine under an atmosphere of nitrogen gave red needles of the enediol, m.p. 192-193°dec. Potassium, salt of 1,2-di-2-quinolyl-l ,2-ethsnediol N,N'dioxide. To a mixture of 1.0 g. of quinaldehyde JV-oxide in 10 ml. of pyridine was added, with stirring, 0.08 g. of potassium cyanide in 2 ml. of water. A white, glistening precipitate, which formed immediately, went into solution after the mixture was stirred for 30 min. at room temperature and refluxed for an equal length of time. Cooling in an ice bath gave a white solid which was crystallized twice from 95% ethanol by adding absolute ether and cooling to give 0.3 g.

Synthesis and Characterization of a Conjugated Polymer with Stable Radicals in the Side Groups

“…4-Bromobenzaldehyde (4) was converted to 4-bromo-3-nitrobenzaldehyde (5) by reaction with a mixture of concentrated sulfuric acid and sodium nitrate, a reaction already used for the preparation of 4-chloro-3-nitrobenzaldehyde. 19 3,4-Dibromobenzaldehyde (6) was prepared by a Sandmeyer reaction. 20 The reaction of aromatic bromides with ethynyltrimethylsilane, using palladium(O) generated in situ as catalyst,21,22 was applied for the conversion of aldehyde 6 to 3,4-bis((trimethylsilyl)ethynyl)benzaldehyde (7).…”