Re: ORGLIST: reducing aldehydes with Raney Ni

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From: Dr Jost T Bohlen (bohlen$##$fiz-chemie.de)
Date: Fri Jun 25 1999 - 03:18:26 EDT

The ChemInform Reaction Library shows two examples in which aluminum
amalgam has been used:
Ehrenstein, M.; Johnson, A. R.; J Org Chem [JOCEAH] 1946, 11, 823.
Brochmann-Hanssen, E.; Jenkins, G. L.; Data, J. B.; J Am Pharm Assoc, Sci
Ed [JAPMA8] 1951, 40, 61.
Unfortunately, in both cases no yields are given.
Another mild procedure with rather good yields using Mg/CuCl2 was
reported more recently:
SARANGI, C.; NAYAK, A.; NANDA, B.; DAS, N. B.; SHARMA, R. P.; Tetrahedron
Lett [TELEAY] 1995, 36 (39), 7119-7122.

I did not find an example of the H2 / Ra-Ni procedure.

Jost T. Bohlen


Eugene Leitl schrieb:

> Hi,
>
> after cutting up my polymer with periodate I get aldehyde-terminated
> ends. To oxidize them I use hydrogen peroxide, autoclaving the product
> to get rid of residual oxidant.
>
> Now I'd like to try something different. Would bubbling hydrogen at
> atmospheric pressure into Raney Ni suspension in polymer solution
> suffice to reduce aldehyde to alcohol? (I tried sodium borohydride,
> it killed the polymer). Is perhaps aluminum amalgam of any value?
> (I can run the thing through a ionic exchange column to trap the
> metal contaminants).
>
> Thanks in advance for your comments.
>
> Regards,
>
> Eugene Leitl
> __________________
>
> ORGLIST - Organic Chemistry Mailing List
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