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Old Sep 23rd 2019, 12:17 AM   #1
NirTau2
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chemoselectivity reduction of sorbic acid to alcohol

Hi everyone, I'm new to the forum.
I'm studying in tau university and I need help to find a cheap way to chemoselectivity reduction of sorbic acid to alcohol. something that will not reduce the conjugate 2,4 double bonds.
without using an expensive reducing agent such as LiAlH4/ LiAlH4/ DIBAL-H/ vitride(red-Al).
I also tried NaBH4 but the yields are low and I need an idea for a catalyst to push the reaction farter more.
I also tried butyl/methyl sorbate, the yield stays low. and using PMHS as reducing agent, that works great, but have very difficult workup.
thank for all the helper. Nir
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Old Oct 2nd 2019, 07:35 AM   #2
Daijo
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My go to for carboxylic acid to alcohol redox is a fast a synthesis of a mixed anhydride and its reduction.

Sorbic acid + hunig's base + (Boc)2O in DCM, filter and concentrate, dissolve in THF add NaBH4 in water to it, quench and extract. Voilą
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