Synthesis and Properties of Optically Active Phenoxypropionates. Effect of Halogeno Substituent in the Core on Physical Properties

Sugita, Shin-Ichi; Toda, Susumu; Yoshiyasu, Takashi; Teraji, Tsutomu

doi:10.1080/10587259308030152

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Cited by 6 publications

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“…We have reinvestigated the long-known reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid [ 22 – 32 ]. The method has been reported for a variety of alcohols, but typically proceeds in aqueous solution and requires an excess of HI or strong mineral acids such as phosphoric or sulfuric acid [ 33 – 35 ].…”

Section: Introductionmentioning

confidence: 99%

Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium

Dobmeier

Herrmann²,

Lenoir³

et al. 2012

Beilstein J. Org. Chem.

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SummaryThe synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene–water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or ether groups are tolerated, and catalytic amounts of hydriodic acid (0.2 equiv) in the presence of 0.6 equiv phosphorous are sufficient to achieve conversion.

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Section: Introductionmentioning

confidence: 99%