hydrolysis of nitrile is very sensitive to the hinderance around the nitrile.
1. KOH in MeOH/water.
140C
2. KOH in ethylene glycol. or diethylene glycol.
200C or 250C.
3. KOH/H2O2/water/EtOH
100C, more reactive toward hindered nitrile.
4. HCl or H2SO4 in water or MeOH
strong acid needed. not compatible with ether, alkene.
5. DIBAlH then oxidation.
6. o-phthalic anhydride.
7. Microwave/ phthalic acid.
8. reductive removal of the nitrile by LidBB or LN, then trap the anion by CO2.
Thursday, June 26, 2008
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3 comments:
Hi,
I am struggling to convert hindered aryl nitrile into an aldehyde. The compound has got sulfonamide - meta to the nitrile moiety. I tried few conditions such as Pd/C, HCOOH (75%), (ii) PtO2, HCOOH (75% V/V) (iii) Aq. H2SO4, H2, Pd/C..Could you please suggest me a condition for this conversion....Cheers Marto
hi, marto
since sulfonamide is very easy to reduce, and you have a hindered nitrile, I can't see any chance to solve your problem.
Sorry I can't help you.
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