How could we synthesize propanol, starting with formaldehyde as the only carbon source?

Question

How could we synthesize propanol, starting with formaldehyde as the only carbon source?

Answer 1

Hope this helps!

I started by reducing formaldehyde to CH3OH using NaBH4 and then turned CH3OH into a Grignard reagent. From there, I reacted 1 equivalent of Grignard reagent (CH3MgBr) to 1 equivalent of formaldehyde which yields CH3CH2OH. PCC oxidizes CH3CH2OH back into an aldehyde, which I can react with another equivalent of Grignard reagent to yield 2-propanol. To transform the product into 1-propanol, I eliminated the alcohol into an alkene and used hydroboration to put the -OH on the least substituted side.