Sciencemadness Discussion Board

Acetylating mandelonitrile?

stygian - 4-6-2006 at 07:35

Last night in a dream, I overheard an elf and a leprechaun saying something about how mandelonitrile could be acetylated at the OH and subsequently at the hydrogen, and that upon hydrolysis, it would turn into hydroxyphenylacetone. Is this true?

Madandcrazy - 4-6-2006 at 09:08

You mean shurely, if it suiteable for some like acetylated syntheses.

But how prepared the diaminomaleonitrile, maybe by
dichloroethylene and a cyanide salt -->
amination, maybe by chlorination -->
diaminomaleonitrile
It is shurely not easy, how handel the fourth binding on the carbon ?
Cl-CH=CH-Cl
Maybe it can prepared by ethylcyanide and oxidized ;) dinitroethylene.

I think the 1,2-dinitril-3,5-dinitraminofuran or something like similar named components are interested within the double bindings and for some imin syntheses.

Some to this, i will get the 1,1-carbonyldiimidazole, it exist some possibillityes with the
usual ;) syntheses ways.

imidazole and dichloromethanone -->
1,1-carbonyldiimidazole

But how prepared the imidazole, by etylenediamin , how can i connect the =C- group
between the amino groups or is it easy prepared by glyoxal and other chemicals.

solo - 4-6-2006 at 09:24

Reference pictorial Information and some.....


mandelonitrile




4-Hydroxyphenylacetone


on other routes discussed see.............

http://www.sciencemadness.org/talk/viewthread.php?tid=1936

[Edited on 4-6-2006 by solo]

Guess I should have said phenylacetylcarbinol...

stygian - 4-6-2006 at 10:38

but anyway.. this is what I was trying to ask.

A known phenylacetone synth is BzCN + EtOAc -NaOMe-> Phenylacetoacetonitrile -H3O+/H2O-> P2P.

My knowledge of such things is vague, but I assume the base is to deprotonate the alpha carbon (thats what you call it right?) so the H can be replaced with C(=O)CH3 (however it is that actually happens), giving the acetoacetonitrile, that I've read hydrolyzes to some intermediate that changes into P2P.

Could mandelonitrile be used instead of phenylacetonitrile? How would the OH affect the reaction? Would the acetylated form react any differently?

Mason_Grand_ANNdrews - 11-6-2006 at 09:17

I guessing the characteristics of mandelonitrile is responsible that mandelonitrile do acetylated to 4-hydroxyphenylacetone and affect to the OH reaction to 4-hydroxy ;).

There are some little misunderstandings in the thread between namings, mandelonitrile, diaminomaleonitrile and some similar chemicals, hydantoin, 2-imidazolidion.

Sandmeyer - 24-6-2006 at 14:23

Quote:
Originally posted by stygian
but anyway.. this is what I was trying to ask.

A known phenylacetone synth is BzCN + EtOAc -NaOMe-> Phenylacetoacetonitrile -H3O+/H2O-> P2P.

My knowledge of such things is vague, but I assume the base is to deprotonate the alpha carbon (thats what you call it right?) so the H can be replaced with C(=O)CH3 (however it is that actually happens), giving the acetoacetonitrile, that I've read hydrolyzes to some intermediate that changes into P2P.


http://www.orgsyn.org/orgsyn/prep.asp?prep=cv2p0487
http://www.orgsyn.org/orgsyn/prep.asp?prep=CV2P0389

see method B in the last link...