[carotis]

hello there! Anyone here has the idea how to create this pharmacon from benzene?

[sjb]

Any thoughts of your own? What functionality is there in the molecule?

[carotis]

well, it looks like a reduced intermediate by wollf kishner... so something happened with benzene, like Friedel Crafts via alcohol then oxidation of this, then Hydrazine? 
How??

[kriggy]

Ok, you already identified some parts of the molecules with possible synthetic pathways. There are two question you need to asnwer:
a) how to make the hydrazino function
b) how to make C-C bond between benzene and the aliphatic part

[carotis]

that's what I want to know. How about Acetyl chloride/AlCl3 with Benzene? Or if someone knows how to substitute  the carbonyl H-atom of the Glycolaldehyde, let me know

[carotis]

hmm... I have to consider the fact that Bromoform could be formed which would give me a C less, so better trying to form a Propionphenone?? I could also first apply Clemmesen reduction but then I have the problem that I don't quite know where the halogene would substitue.. just can't get it done 
I have decided on F.C reaction to Acetophenone, then radical bromation, then Clemmesen reduction, then substitute Br with H2O so this could react with Hydrazine to the product.
Would it make any sense? It was some time I occupied myself with organic synthesis ^^

[AWK]

https://www.wikiwand.com/en/Ethylene_oxide

[carotis]

how abot this?
Glycolic acid + SOCl2 => reaction of benzene to Glycolophenon => +H2N-NH2 => product.
Would it work?

[carotis]

no, this is bs... Hydarzine wouldn't react with a Hydroxgroup, is that right? First I should transform the OH group with PBr3 to alkyle bromide

[kriggy]

You could possibly use mitsunobu reaction. But there is a problem that you might get the hydrazine substitued on both nitrogens