Phenyl glycidyl etherとアルコール, チオールの反応

概要

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The reaction of phenyl glycidyl ether with ethanol at about 80° in the presence of sodium hydroxide, sodium ethoxide, or triethylamine afforded mainly 1-ethoxy -3-phenoxy-2-propanol in 50-65% and 2-ethoxy-3-phenoxy-propanol in only 1.8%. By the identification of oxidative products of these compounds with 1-ethoxy-3-phenoxy-2-propanone or 2-ethoxy-3-phenoxypropionic acid, which was obtained by another independent synthetic method, the structures of these compounds was proved to be the primary or the secondary alcohol mentioned above. The reaction of phenly glycidyl ether with ethanol in the presnece of sulfuric acid resulted in the increase of primary alcohol. Without the catalyst, the reaction velocity was very low and at elevated temperature, a large amount of 3-phenoxy-1,2-diethoxypropane was formed. Thioethanol reacted well with phenyl glycidyl either even at lower temperature than ethanol did and afforded 1-ethylthio-3-phenoxy-2-propanol. Higher thiols, however, showed poorer yields. The reaction of phenyl glycidyl ether with dialkylaminoethanol or dialkylaminothioethanol also gave corresponding basic etheralcohols. When phenylthioglycidyl ether was reacted with ethanol or thioethanol, 1-ethoxy-3-phenylthio-2-propanol or 1-thioethyl-3-phenylthio-2-propanol was obtained in a good yield. These compounds are expected to be effective as a muscle relaxant.
公益社団法人日本薬学会の論文
1968-01-25