Pages

▼

Thursday, June 26, 2008

Nitrile to acid

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.
at

3 comments:

  1. martoAugust 13, 2008 at 3:09 PM

    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

    ReplyDelete
  2. Weiwei TIANAugust 13, 2008 at 6:20 PM

    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.

    ReplyDelete
  3. AnonymousFebruary 14, 2010 at 4:42 PM

    Nice post and this fill someone in on helped me alot in my college assignement. Say thank you you for your information.

    ReplyDelete

Your comments are welcome.