[zilallti]

Hello all,

I carried out this synthesis in my group a few years ago (attached), however, I'm a physical chemist and am scratching my head trying to work out the mechanism.

Am I right in thinking it is Henry's reaction? I.e I would guess that there is a removal of hydrogen on the ethyl carbon creating a carbanion (stabilized by resonance in the nitrobenzene ring) which attacks aldehyde to form the product. But wouldn't this need a base to proceed?

Thanks!

[clarkstill]

Do you know the structure of Triton-B?

[zilallti]

Ah so the triton B acts a base too? I assumed it was just a phase transfer catalyst

[clarkstill]

Yeah I reckon. I suppose a pedant might say it isn't quite a Henry reaction, since this is generally a reaction involving a nitroalkane, rather than a nitroaromatic, but your proposed mechanism sounds legit.

[zilallti]

Thanks!