Author Topic: Synthesis Question.  (Read 448 times)

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cattleprodder

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Synthesis Question.
« on: April 15, 2003, 02:42:00 AM »
Can anyone figure out how to make 4-ethyl-3-methoxybenzaldehyde?

Rhodium

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4-alkyl-3-alkoxybenzaldehydes
« Reply #1 on: April 15, 2003, 02:34:00 PM »
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.