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solo
International Hazard
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Reference Information
Mild Reduction of Carboxylic Acids to Alcohols Using Cyanuric Chloride and Sodium Borohydride
Massimo Falorni,* Andrea Porcheddu and Maurizio Taddei
Tetrahedron Letters 40 (1999) 4395-4396
Abstract
Several carboxylic acids, including N-Boo, N-Cbz and N-Fmoe amino acids were reduced to the corresponding alcohols by activation of the carboxy
function with cyanuric chloride and N-methylmorpholine followed by reduction with aqueous sodium borohydride.
Keywords: Reduction, Carboxylic acids, Alcohols, Amino acids.
Attachment: Mild Reduction of Carboxylic Acids to Alcohols Using Cyanuric Chloride and Sodium Borohydride .pdf (125kB)
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It's better to die on your feet, than live on your knees....Emiliano Zapata.
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haribo
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My god, this is getting complecated. Is there something wrong with SOCl2? It's very cheap, every single chem-source carries it and it's really well
documented.
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Sauron
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thionyl chloride
The problem is political. SOCl2 has been demonized because Saddam used it to chlorinate thiodiglycol (now likewise demonized) to make HD "German"
style in vast quantities to toss at the Iranians and sometimes his own people. Now, thionyl chloride is a CWC-scheduled chemical subject to
international controls. Sure every chem supplier lists it but have you tried to buy any in the last few years?
Other classical chlorinating reagents also on the no-go list are PCl3 and PCl5. And POCl3. And red P is also banned, in addition to being on the DEA
watchlist because of meth cooks AND being a pyrotechnic material thus making the anti-terrorist forces skittish.
Hence, greatly increased interest in viable, still accessible alternatives for when one must chlorinate a hydroxyl group or a carboxylic acid.
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manimal
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Sorry to resurrect this thread, but wouldn't ZnCl2 form a complex with the amino alcohol, thus interfering with chlorination?
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