Preparation of Novel Dideuterioallyl Mercaptan

A difference in mass units of two or more gives the best results in the quantitative determination of each ingredient. In order to analyze the allyl mercaptan present in the odor of bulgogi (a popular Korean dish) we needed to have allyl mercaptan-1,1-d₂ or allyl mercaptan-2,3-d₂. Neither compound has been reported in the literature. One of the logical schemes for the synthesis is to preparing corresponding allyl alcohol and converting it to the corresponding mercaptan. Allyl alcohol-d₅ (Cd₂=CDCd₂OH) is commercially available, but the -1,1-d₂ or -2,3-d₂ alcohol is not. Allyl alcohol-1,1-d₂ has been reported to be prepared by reduction of acryloyl chloride with LiAlD₄. There are numerous citations of the use of LiAlH₄ for the reduction of α,β-unsaturated carboxylic acids to alkenols. For example, a reference book states that lithium aluminum hydride reduces exclusively the carbonyl group, even in an unsaturated acid with α,β-conjugated double bonds