cattleprodder (Hive Bee)
04-15-03 02:42
No 426750
      Synthesis Question.  Bookmark   

Can anyone figure out how to make 4-ethyl-3-methoxybenzaldehyde?
(Chief Bee)
04-15-03 14:34
No 426937
      4-alkyl-3-alkoxybenzaldehydes  Bookmark   

The only feasible route I've seen in the literature involves starting with the 4-alkylbenzaldehyde, nitrating it in the 3-position, reducing the nitro and the resulting amine converted sandmeyer style to the phenol which is then alkylated.

You might be able to brominate the 4-alkylbenzaldehyde (adding elemental bromine to a mixture of the aldehyde and AlCl3 according to preparations of similar compounds in Organic Syntheses) and then methoxylate this with sodium methoxide with catalytic CuBr or CuI.

You might need to protect the aldehyde as the acetal for some of the steps.

4-alkyl-3-alkoxybenzaldehydes are incredibly scarce in the literature.