Vanillin is easily brominated by Br2 to give 5-Br-vanillin in good yield. Ethoxylation of the resultant compound has been attempted numerous times via reaction with quantitative and 1.3 equivalents of Na/KOH in EtOH and freshly distilled EtBr or gaseous EtBr generated via dripping H2SO4/EtOH onto a saturated solution of NaBr in H2O. The upon dissolution of the substrate, a whitish precipitate always forms and does not go back into solution, despite heavy stirring and attempts with mild heating.

The reaction workup consists of diluting the reaction matrix with basic water in order to precipitate the non-polar product, but this always fails.

Ethoxylation was attempted on vanillin once preceding the bromination, but this method was abandoned due to the directing effects of the ethoxy group versus the phenol group: http://www.erowid.org/archive/rhodium/chemistry/tma2.vanillin.html

Eugenol may be another viable starting material, but the reaction with bromine, which requires a phenol moiety to add to the correct position of the ring, cannot be carried out without first doing something about that allyl chain. Amination has been considered for the first step, but then the reaction with EtBr is not feasible (the amine will react instead of the phenol). (Pseudo)Nitrosation is being considered, but there is major concern that the double bond behind the nitro group will just react with the EtBr.

Input is greatly appreciated.

No you wouldn't get TMA you would get the PEA form of it. This has already been talked about here.

You will get very little EtBr by dripping H2SO4 and EtOH onto NaBr solution if any. More then likely your just going to generate alot of Br2.

Have you tested the white precipitate to see if its Sodium or Pottasium bromide?

No, Sedit,

beta-phenylnitroethane reacts with dimethylcarbonate to yield alpha-methyl, beta-phenylnitroethane. A common error among less-informed chemists is that amphetamines can be made from the Henry reaction with nitromethane (they can't, you need nitroethane); but with this process it would be much more practical to make phenylisopropylamines from reaction with nitromethane and DMC. 2 immediately obvious options:
1) Partial reduction of the olefin followed by reaction with DMC. Then reduction of the nitro group. Hydrogenation by 2 different methods should be able to achieve both tasks (perhaps even a simultaneous approach could be worked out since one would likely be working with pressure, which is how DMC usually reacts--massive potential here provided someone can assure me that in nitroalkene reductions, the olefin is targeted first, or that a practical hydrogenation reaction exists that would allow that to occur).
2) Full reduction to the ethylamine, then oxidation to the nitroethane, reaction with DMC, and reduction back to the amine (the interconversion between the 2 oxidation stages of the nitrogen can be nearly quantitative with several OTC reagents, making this process particularly useful although more tedious).

I'm still seeing if it's possible to do this with the alkene alone but that was the point I was trying to get across.

No, Sedit,

beta-phenylnitroethane reacts with dimethylcarbonate to yield alpha-methyl, beta-phenylnitroethane. A common error among less-informed chemists is that amphetamines can be made from the Henry reaction with nitromethane (they can't, you need nitroethane);

Im abit confused but it appears along the same lines as what I was stating before. You can not make TMA thru the Henry reaction with MeNO₂. Did I miss something?

Wait are you suggesting methylating the nitrostyrene with DMC?

I believe the documents your looking for are works of Demonic over at the hyperlab if that helps any.

Q_D: http://www.sciencemadness.org/talk/files.php?pid=97788&aid=3247

Sedit, the suggestion is to reduce the nitroalkene and alkylate the nitronate. So far as I know, this is less practical than desired but there may be a way to the amphetamine using something akin to this route.

eugenol + KOH -->
3-MeO-4-NaO-phenyl-2-OH-propane + X2 -->
3-MeO-4-NaO-5-X-phenyl-2-OH-propane + EtBr -->
3-MeO-4-EtO-5-X-phenyl-2-OH-propane + KMnO4 or dichromate -->
(blah blah) ketone + hexamine --> titular/desired compound

The main concerns is in the first reaction, as the substituted allylbenzene may be labile to a rearrangement from a 2-substituted phenylpropane to a 1-substituted isomer.

Any thoughts/input/suggestions?

Ahh whoops haha. First add HX, then base.