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What are the different ways of transforming a carboxylic acid into an aldehyde in a single step ? (as opposed as for instance first transforming it to an ester then to an aldehyde)

The bottom of this page doesn't indicate any such way.

I am not looking for a "big-list", so the most common ways would be enough.

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  • $\begingroup$ DIBAL is the best way I know of. $\endgroup$ – SendersReagent Mar 26 '16 at 19:04
  • $\begingroup$ @DGS The link in my question says that DIBAlH reduces it to alcohols. Hence the 'need' to transform it into an ester before using DIBAlH $\endgroup$ – Hippalectryon Mar 26 '16 at 19:09
  • $\begingroup$ You're right. There are instances of success, but it's not as good as I thought. $\endgroup$ – SendersReagent Mar 27 '16 at 2:19
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$\ce{Li, RNH2 (R=Me, Et)/NH4Cl/H3O+}$

$\ce{BH3.SMe2/PCC}$

$\ce{(CH3)2CHC(CH3)2BH2}$

$\ce{(CH3)2CHC(CH3)2BHCl.SMe2}$

$\ce{(CH3)2CHC(CH3)2BHBr.SMe2}$

9-BBN/Li 9-BBN

9-BBN/t-BuLi/9-BBN

DIBAL-H

  • Zakharkin, L. I.; Khorlina, I. M. Zh. Obshch. Khim. 1964 34, 1029; J. Gen. Chem. USSR 1964 34, 1021.

bis(N-methylpiperazinyl)aluminum hydride

activated silyl carboxylates

titanium-catalyzed Grignard

N,N-dimethylchloromethyleniminium chloride and lithium tri-t-butoxyaluminum hydride

$o\text{-}\ce{HSC6H4OH, POCl3, HClO4/LiAlH4/H2O, HgCl2}$

$o\text{-}\ce{(NH2)C6H4, PPA/NaOet/MeI/NaBH4}$ or $\ce{LiAlH4/H3O+}$

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    $\begingroup$ But @Hipp didn't ask about big list ;) $\endgroup$ – Mithoron Mar 27 '16 at 20:51

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