How do I make acetophenone from benzaldehyde?

1 Answer
anor277
May 6, 2017

Efficiently.......?

Explanation:

You must increase the carbon chain by one........

#C_6H_5C(=O)H rarr C_6H_5C(=O)CH_3#

The obvious route is by the Grignard reagent methylmagnesium iodide, which gives the #2^@# alcohol (after work up), and then the alcohol is oxidized up to acetophenone:

#(i)# #C_6H_5C(=O)H +MeMgIstackrel"dry ether"rarr C_6H_5CH(-O^(-))(Me)#

#(ii)# #C_6H_5CH(-O^(-))(Me) stackrel(H_3O^(+))rarr C_6H_5CH(OH)(Me)#

#(iii)# #C_6H_5CH(OH)CH_3 stackrel(KMnO_4"/"H_3O^+)rarrC_6H_5C(=O)CH_3#

The oxidation step is a little bit fierce, but you should get away with it.

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