Sciencemadness Discussion Board

reduction of carboxylic acid without hydride

smartgene1 - 23-12-2016 at 11:14

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]

Magpie - 23-12-2016 at 12:45

The Bouveault-Blanc rx will take an ester to an alcohol using sodium.

DJF90 - 23-12-2016 at 13:02

How about a Hunsdeicker reaction to the alkyl halide, Grignard formation, and subsequent reaction with formaldehyde?

NitreRat - 23-12-2016 at 17:16

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]

Magpie - 24-12-2016 at 10:15

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.

gdflp - 24-12-2016 at 10:32

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.

Magpie - 24-12-2016 at 10:33

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.

CuReUS - 25-12-2016 at 08:07

http://pubs.acs.org/doi/abs/10.1021/ol203361k