Summary
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1.
In acid hydrolysis 2-cyanoethyl ethers of acetylenic alcohols are almost completely resinified, and in alkaline hydrolysis the expected 2-carboxyethyl ethers of acetylenic alcohols are obtained, but in poor yiled (30–40%).
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2.
2-Carboxyethyl ethers of acetylenic alcohols are formed smoothly and in good yield (76–94%) by the hydrolysis of the readily accessible 2-(methoxycarbonyl) ethers of acetylenic alcohols by treatment with aqueous-methanolic sodium hydroxide at room temperature.
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3.
In order to be able to test their physiological, particularly soporific, activities, some amides of 2-carboxyethyl ethers of acetylenic alcohols were synthesized by the action of ammonia or amines on the corresponding acid chlorides.
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