How to Convert Acetic Acid to Propanoic Acid Without Cyanide?

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Acetic acid can be converted to propanoic acid through methods that avoid cyanide, with acetyl chloride and N-methylethanamide being initial considerations. However, challenges arise in removing nitrogen and introducing a hydroxyl group. One proposed solution involves using acetyl chloride followed by diazoketone and Wolff rearrangement, ultimately adding water. The discussion highlights the complexity of chain homologation and the need for precise structural transformations. Overall, alternative pathways for this conversion are being explored, emphasizing the intricacies of organic synthesis.
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Without using a cyanide
 
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What other methods of chain homologation do you know?
 
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?
 
Can you draw some structures? Seems like N-methylacetamide has the wrong carbon backbone too.
 
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?
 
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