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29.6.1.2.5.1 Variation 1: With Other Acetals

DOI: 10.1055/sos-SD-029-00368

von Angerer, S.; Warriner, S. L.Science of Synthesis, (200729341.

When two different acetals react in the presence of an acidic catalyst such as 4-toluenesulfonic acid, an interchange of the alcohol components occurs which affords a mixture of acetals derived from different alcohols and/or different carbonyl compounds.[‌285‌,‌327‌‌329‌] From a preparative point of view, this reaction is not always useful. However, when an acetal formed by two different alcohols is treated with a catalyst, symmetrical acetals are formed. If one of these is sufficiently volatile it can be removed in the course of the reaction whilst the other symmetrical acetal accumulates (Scheme 52).[‌121‌] This reaction can also be used to exchange the protecting group of an alcohol. When decyl tetrahydropyranyl ether is treated with dimethoxymethane in the presence of zirconium(IV) chloride, the tetrahydropyranyl group is almost quantitatively replaced by the methoxymethyl group.[‌330‌]

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