smartgene1
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reduction of carboxylic acid without hydride
Is there anything out there that is strong enough to reduce carboxylic acid to an alcohol without a hydride or hydrogenation
[Edited on 23-12-2016 by smartgene1]
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Magpie
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The Bouveault-Blanc rx will take an ester to an alcohol using sodium.
The single most important condition for a successful synthesis is good mixing - Nicodem
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DJF90
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How about a Hunsdeicker reaction to the alkyl halide, Grignard formation, and subsequent reaction with formaldehyde?
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NitreRat
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Conversion to an amide, dehydration to a nitrile, and reduction with SnCl2/HCl to an aldehyde?
EDIT: Acyl halides and anhydrides are easier reduction targets if you can make them.
[Edited on 12/24/2016 by NitreRat]
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Magpie
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Quote: Originally posted by DJF90  | | How about a Hunsdeicker reaction to the alkyl halide, Grignard formation, and subsequent reaction with formaldehyde? |
Once you have the alkyl halide in some cases you may be able to go directly to the alcohol via SN2 using NaOH.
The single most important condition for a successful synthesis is good mixing - Nicodem
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gdflp
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| Quote: Originally posted by Magpie |
Once you have the alkyl halide in some cases you may be able to go directly to the alcohol via SN2 using NaOH. |
The Hunsdeicker reaction removes a carbon, so you need the Grignard to re-extend the carbon chain.
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Magpie
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Yes, I see. That assumes he needs that carbon. Hopefully, he won't need to do that, though, as addition of a carbon via use of formaldehyde/Grignard
can be a real PITA. I know because I've done it.
The single most important condition for a successful synthesis is good mixing - Nicodem
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CuReUS
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http://pubs.acs.org/doi/abs/10.1021/ol203361k
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