Synthesis of 4-MethyPropiophenone?

[bigdigrandy]

Hello fellow chemistry enthusiasts,

I have personally not looked to much in the preparation of 4-Methylpropiophenone.

I have thought of a synthesis of it using succinic anhydrid on toluene using a simple Friedel–Crafts reaction with Aluminum Chloride as a catalyst, yielding 4-(4-methylphenyl)-4-oxobutanoic acid which is then decarboxylated to 4-Methylpropiophenone. The precursors seem to be widely available and relatively cheap.

If someone knows more about potential yields, or mistakes I made please let me know, because I might try it out myself.

 

[The_Real_DEA_42069]

I don't think this is gonna work the way you're wanting it to bc the oxobutanoic acid is a gamma ketone, not a beta ketone.

You could give CuO a shot, it seems to work for levulinic acid

Oxidative Decarboxylation of Levulinic Acid by Cupric Oxides

 

[The_Real_DEA_42069]

I've never tried it myself, but I just looked and the tolyloxobutanoic acid is available from a well-known chemical vendor for $150 for 100g. No idea about yield following CuO but on the surface it certainly sounds like it beats a propionyl chloride and methyl propiophenone synth. Might have to give it a shot one of these days.

 

[Osmosis Vanderwaal]

Usually it's toluene and propoinyl chloride with aluminum chloride Friedel-kraft.
Please, use the search engine

 

[Osmosis Vanderwaal]

This patent lays out a lot of substituted propriophenone synthesis

US4690931A - Therapeutically useful 1-phenyl-2-piperidinoalkanol derivatives - Google Patents

Compounds of the formula: ##STR1## wherein R 1 is hydrogen, halogen, trifluoromethyl, alkyl, hydroxyl, alkyoxy, benzyloxy, alkanoyloxy, or benzoyloxy, or when R 2 is hydroxyl or methoxy in the 4-position and R 3 is hydrogen, R 1 may also represent hydroxymethyl carbamoyl or alkoxycarbonyl...

patents.google.com

 

[The_Real_DEA_42069]

My comments are, of course, speculative retrosynthesis — I would always recommend first the given default procedure of synthesizing the substituted propiophenone via AlCl3 F-K with toluene and propionyl chloride or the anhydride if one isn't absolutely clear on what's being discussed in theoretical alternative routes