In order to extend a previous investigation on glycol mercurials,1 through the introduction of a phenyl group into the glycol molecule, a series of glycols containing a substituted or an unsubstituted phenyl group, was prepared. The commercially available 2-phenoxyethanol, C6H6-OCH2CH2OH, the monophenyl ether of ethylene glycol, was selected as a suitable aromatic glycol which would lend itself readily to variations in structure.The basic structure was varied in three ways:(I) extension of the side chain, CeHeCOCK^CHi)*-OH; (II) substitution in the ring, p-XCeHr OCH2CH2OH, where X is CH3, Br, OH, N02, NH2;(III) introduction of another /3-hydroxy-ethoxy group into the ring, HOCH2CH2OC6H4OCH2CH2-OH.the general method of treating the sodium salt of the appropriately substituted phenol in absolute alcohol with ethylene chlorohydrin.3The mercurials which were prepared from the aromatic glycols listed herein are reported in the paper immediately following.
Derivatives of 1,3-Di-(^-hydroxyphenyl) -propane 1579 4-hydroxyphenyl)-ethane, in common with hexestrol, are geometrically related to estradiol but, in contrast, have no estrogenic activity.2. The amino analog of hexestrol, 3,4-bis-(£aminophenyl)-hexane, is inactive.3. Replacement of the ^-hydroxyphenyl groups of hexestrol with 3,4-dihydroxyphenyl or p-hydroxybenzyl results in decreased estrogenic activity.Pearl River, N. Y.
Dialkyl Derivatives of 1 ,3-Di-(P-hydroxyphenyl) -propane 1475 ml. of dry ether. A crystal of iodine was added, followed by 1 ml. of ethyl bromide. As soon as the reaction had started, the stirrer was turned on, a slow stream of dry nitrogen was passed through the flask and 60 g. (0.4 mole) of l-diethylamino-3-chloropropane, dissolved in 100 ml. of dry ether, was added over a period of ten minutes. Another ml. of ethyl bromide was added, the flask was heated in a water-bath vept at 45-50°for five minutes and then 27.2 g. (0.2 mole) of anisaldehyde, dissolved in 160 ml. of dry ether,1? was added over a period of ninety minutes. The stirring, heating and nitrogen flow were continued during the addition and for twelve hours after the addition was complete. A white precipitate formed.9 10 After standing overnight the reaction mixture was hydrolyzed by a solution of 75 g. of ammonium chloride in 200 ml. of water.
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