2,5-dimethoxy-4-methylbenzaldehyde

lemuralia · Mon Aug 08, 2005 9:41 pm

Is there anyway to methylate 2,5-dimethoxy-benzaldehyde into 2,5-dimethoxy-4-methylbenzaldehyde?

The only way SWIM could find of producing 2,5-dimethoxy-4-methylbenzaldehyde is from Shulgin's write-up. But that requires POCl3.Thanks.

anime · Mon Aug 08, 2005 9:53 pm

you could perform a reduction on the 2,5-dimethoxybenzaldehyde yo 2.5-dimethoxytoluene and then formylate that. Or you could start with Methylhydroquinone and O-methylate that and then go on to the formylation.

Formylation is the hard part.

fogged · Fri Aug 12, 2005 8:38 pm

You could also brominate the 2,5-dimethoxybenzaldehyde in the 4 position, followed by reacting it with n-butyl lithium in dry THF, and finally adding methyl iodide or similar. Of course, that'd have to be done at around -78C (dry ice/acetone bath). But it should definitely work if you have access to these things!

icecool · Insistent Chemist

Can you adjust the place where to brominate 2C-H?
And if so what effects would it have on the effect of the drug itself...
And how would you adjust the place of addition of bromine, temperature?

anime · Sun Aug 14, 2005 12:16 am

the only other place that bromine will go is the 6th position. It forms in small amounts when you brominate 2,5-dimethoxybenzaldehyde.