Synthesis of Pentitols from Unsaturated Intermediates

Very little work on the synthesis of pentitols had been carried out before 1928. Those pentitols which had been synthesized were made by the reduction of pentoses. Several pentitol intermediates had been synthesized and it seemed desirable to attempt to complete the synthesis of pentitols from the unsaturated intermediates, using the methods which had been successfully employed in the synthesis of hexitols. 

The desired intermediates, pentadienol or a pentenetriol were unknown at the time, but it occurred to me that their synthesis might be accomplished by the partial reduction of a pentenynol or a pentynetriol, the latter being obtained from the reaction of one molecule of acrolein or acrolein dichloride with the Grignard reagent derived from acetylene. The reactions which have been carried out in accordance with this scheme are shown in the accompanying flow sheet. 

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III. Synthesis of Pentitols from Unsaturated Intermediates 1. Methods of Preparation... 

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