How to Convert Acetic Acid to Propanoic Acid Without Cyanide?

[deep838]

Without using a cyanide

 

[sjb-2812]

What other methods of chain homologation do you know?

 

[deep838]

i was thinking of acetyl chloride and then N-methylethanamide... that will give me 3 carbons... but then how to get rid of nitrogen and bring OH?

 

[sjb-2812]

Can you draw some structures? Seems like N-methylacetamide has the wrong carbon backbone too.

 

[deep838]

yeah... that's where I'm stuck... i really have no idea on how to bring the carbon inside!

how about this:
acetyl chloride then diazoketone then wolff rearrangement and then water! right?