October 16, 2019, 08:09:22 AM
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Topic: chemoselectivity reduction of sorbic acid to alcohol  (Read 210 times)

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Offline nir.tau2

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chemoselectivity reduction of sorbic acid to alcohol
« on: September 22, 2019, 07:40:30 AM »
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. thank for all the helper. Nir

Offline kriggy

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Re: chemoselectivity reduction of sorbic acid to alcohol
« Reply #1 on: September 22, 2019, 09:23:48 AM »
Borane might work there. You might need to convert the acid into ester but its used to reduce amino acid into amino alcohols

Offline OrganicDan96

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Re: chemoselectivity reduction of sorbic acid to alcohol
« Reply #2 on: September 22, 2019, 09:42:43 AM »
how about luche conditions, Cerium chloride and sodium borohydride

Offline kriggy

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Re: chemoselectivity reduction of sorbic acid to alcohol
« Reply #3 on: September 22, 2019, 10:38:34 AM »
Do they work for acids or esters though? It might be worth trying as well

Offline rolnor

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Re: chemoselectivity reduction of sorbic acid to alcohol
« Reply #4 on: September 22, 2019, 04:40:58 PM »
Is LAH more expensive then NaBH4 or borane?

Offline hollytara

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Re: chemoselectivity reduction of sorbic acid to alcohol
« Reply #5 on: September 22, 2019, 06:00:25 PM »
Borane does work with acids - but it is a bit more difficult to work with.

I have reduced methyl esters with potassium borohydride in THF with lithium chloride as a catalyst.  If you can make the methyl ester, it's pretty gentle but effective.

Offline rolnor

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Re: chemoselectivity reduction of sorbic acid to alcohol
« Reply #6 on: September 23, 2019, 03:36:45 PM »
There is no cost advantage with these suggestions, LAH is not expensive in comparison.

LAH 25g 40USD Mw 37,95
Borane 1M in THF 100ml 40USD
KBH4 5g 58USD Mw 53,94
CeCl3 5g 100USD Mw246,48
NaBH4 25g 36USD Mw37,83

Prices are aprox. From Aldrich

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