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Synthesis of α-hydroxy phosphonates

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An efficient and simple synthesis of α-hydroxy phosphonates has been achieved via reaction of aldehydes with trimethylphosphite in the presence of Amberlyst-15 in water. The reaction is highly selective with excellent yields under mild conditions.
M. Tajbakhsh, A. Heydari, M. A. Khalilzadeh, M. M. Lakouraj, B. Zamenian, S. Khaksar, Synlett, 2007, 2347-2350.


A very convenient reaction of trialkyl phosphites with aldehydes or ketones in the presence of hydrogen chloride gives dialkyl 1-hydroxyalkylphosphonates in good yields via an Arbusov-like reaction of oxonium salts derived from aldehydes or ketones. This reaction is an alternative to the well-known Abramov reaction.
W. Goldeman, M. Soroka, Synthesis, 2006, 3019-3024.