[egilbreth]

(Br₂,hv) (NaOH, Δ) (H₂SO₄,H₂O) (CrO₃, H₂SO₄) (Δ) +

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  (H₂,Ni) (H₂SO₄, Δ) (H₂,Ni)

I think it's possible but I was unsure if there would be problems when trying to brominate the original acid and if adding a ketone to split it like that would even be possible. Any feedback is much appreciated

[rolnor]

There are many steps one could comment but the fifth step is questionable, what you have is pyruvic acid but you draw it as an enol-form;
https://en.wikipedia.org/wiki/Pyruvic_acid

One thing that could be very difficult is the work-up, you have very polar compounds and H2SO4 and cromium-salts, have you thought about that? Also I see risc of decarboxylation in some steps.

[egilbreth]

With respect to the pyruvic acid would it be possible to preform a wolf-kishner to eliminate the ketone instead of what I did in the bottom section? Or just to clarify would the pyruvic acid automatically decarboxylate because of the β carbonyl group?
Also would PCC work better than the H2SO4 and cromium-salt or does that run into the same issue because of the polar compound and acid

[Babcock_Hall]

How do you plan to control the stoichiometry in the first step?

[wildfyr]

That's a hell of a way to make acrylic acid hahaha. Avaikabke for about $30 a kg