[reallymissinvine]

Post-grad professional here working in R&D. I haven't done ochem in a little while, but I wanted to ask and see if someone could give some insight into my theoretical procedure.

Starting material: tryptophan/W (let's just estimate 5 g)

1. React W with α-ketoglutarate in 2 eq of 6M HCl to yield indole-3-pyruvic acid.
2. purify the product with liquid-liquid extraction
3. React indole-3-pyruvic acid with LiAlH₄ in H₃O⁺ to yield 3-indolecarbinol.
4. Purify with (not sure on technique here).
5. Treat indole-3-carbinol with DMP (quantity unknown) to form indole-3-acetaldehyde.
6. Purify with (not sure on method here).
7. Treat indole-3-acetaldehyde with H₂CrO₄ to yield indole-3-acetic acid.

What would you change/add? Any considerations I should take into account? I know that some of the reagents here are strong oxidizing/reducing agents, but I don't remember working with them in ochem 1 or 2. Also obligatory "not-a-chemist," I am a biology graduate with a minor in chemistry.

[Babcock_Hall]

What is the intended use, and why are you making something that can be purchased for a low price?  This is a long synthesis for someone who is not doing synthetic chemistry on a daily basis.  If I were obliged to make it, I would look up previous syntheses using SciFinder Scholar or some equivalent tool.

[reallymissinvine]

I was mainly looking at the synthesis out of curiosity. I had found it on Sigma already, but I was interested in the actual lab steps someone would need to do to make it.

[Babcock_Hall]

I would look into methods which convert an alcohol directly into an acid, which would save a step.  Then I would compare with what is in the literature.