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25.1.5.1 Method 1: Synthesis from Halohydrins

DOI: 10.1055/sos-SD-025-00101

Kalesse, M.Science of Synthesis, (200725137.

Halohydrins serve as a formidable starting point for the generation of aldehydes through a rearrangement. One of the major advantages of this transformation is that the corresponding halo ketones, e.g. 2, can be derived from a [2+2] cycloaddition of dichloroketene to alkenes, e.g. 1 (Scheme 1). Reduction of the ketone carbonyl group provides the starting point for the rearrangement of halohydrin 3 (Scheme 1).[‌1‌] Subsequent reductive removal of the chloride in α-chloroaldehyde 4, to give aldehyde 5, can be achieved in low yields with zinc in boiling acetic acid.

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