Before i even start, the reaction itself and notes are copypasta mostly from SM. Klute from SM is to who my hats goes, he put me onto this an it sparked some interest in me.

I followed this :

a) http://www.apc.titech.ac.jp/~tikariya/mito/teaching/2005/textbook.pdf
b) http://www.sciencemadness.org/talk/viewthread.php?action=attachment&tid=9706&pid=113977


The synthesis itself is nice and simple and yields are nice. The product smells nice, i will try to do the hydrogenation next week :)

Here we go:

Synthesis of 1-(4-hydroxy-3-methoxyphenyl)but-1-en-3-one by basic crossed-aldol condensation of vanillin and acetone

note: your suppose so stir the reaction for all the 24 hours, but my mag stirrer was K.O, so i shook it every 5 hours, got a little smaller yield but its ok :)

In a 125 ml beaker was placed 5 g of reagent grade vanillin:
http://img102.imageshack.us/img102/5082/img0499xf6.jpg

20 ml of Acetone (distilled and dried) where measured out:
http://img49.imageshack.us/img49/8809/img0500px1.jpg

20 ml of previously measured acetone where placed in the beaker (with the vanillin) and it was stirred until it was fully dissolved into a colorless/slightly yellow solution:
http://img48.imageshack.us/my.php?image=img0501hn6.jpg

The just made solution was caped and placed aside while the rest was prepared:
http://img49.imageshack.us/my.php?image=img0503ga3.jpg

2g of NaOH were dissolved in 20mL dH2O (10% w/v) and the solution was cooled under a stream of water and transferred to a 50 ml additional funnel
http://img48.imageshack.us/my.php?image=img0504ai7.jpg

The addition was began at around 3 drops per second, little heat was evolved from this addition:
http://img247.imageshack.us/my.php?image=img0506ma1.jpg

Nearly finished adding all:
http://img247.imageshack.us/img247/294/img0508yg3.jpg

Addition finished +5 min passed:
http://img361.imageshack.us/my.php?image=img0512mr5.jpgg

After 10+ min passed, the beaker was covered in aluminum foil and placed aside:
http://img365.imageshack.us/my.php?image=img0514ew1.jpg

After ~20 min passed (notice the dark red color). It was left like this for 24 hours:
http://img141.imageshack.us/my.php?image=img0515ga2.jpg

After 24 hrs passed a 100mL of 3M HCL was prepared and slowly added with vigorous stirring (Notice how the now the vanilla+acetone+NaOH sol has turned dark, nearly black, next to it the HCL:
http://img229.imageshack.us/my.php?image=img0527ix7.jpg

Upon the addition of the HCL, the solution in the beaker turned a dark turgid yellow and a large amount of yellow solids crashed out, stirring was continued for 5 min and the beaker was then left another 10 min alone to allow everything to settle:
[http://img146.imageshack.us/img146/3961/img0529gy0.jpg/IMG]

I set up for vacuum filtration but my vacuum pump had some problems, so gravity filtration was done :mad::
[IMG]http://img512.imageshack.us/my.php?image=img0531ma0.jpg

Finishing filtering:
http://img98.imageshack.us/my.php?image=img0534jj8.jpg

Filtrate was placed in a beaker and dissolved in a minimal amount of warm EtOH:
http://img80.imageshack.us/my.php?image=img0537od6.jpg

Finished evaporating:
http://img516.imageshack.us/img516/7214/img0547bl2.jpg

Ta daaah:
http://img227.imageshack.us/img227/6459/img0550on1.jpg

Final yield was 4.8 g which means a ~78% yeild, not too bad considering i had no stiring, if you look at Klute crystals on SM they look a lot nicer :( That is because i couldn't vacuum filtrate it properly :mad:

Next step is hydrogenation which will be performed as in the paper but with 8% Cu/SiO2
[ http://www.sciencemadness.org/talk/viewthread.php?tid=10704 ],
its nice because its on pyrophoric or pyrogenic catalyst and can be recycled, cheaper then 10% Pd/C, raney nickel or any other. This can open the doors to hydrogenation at atm pressure to the average home chemist :), if Cu/SiO2 doesn't work then 10% Pd/C will be used :(

That's shit hot! I may well have a go at that if I can find a sauce for vanillin. It's lazy as hell, but seen as though the reaction appears to be done in aqueous media, if the acetone was of decent quality, distilled, but not dried, there wouldn't be any negative effects on the reaction?

Interestingly enough, there are plenty of other naturally occurring organics, based around benzaldehyde with similar organic groups, I wonder what results would be like if a similar synthesis was done on a different substrate/precursor molecule?

Edit ; does it actually smell like raspberries?
Edit 2 ; Lies and fallacy you fucking cunt! The tags!

Klute's been around for time now and is, from what I've seen, reliable, helpful and knowledgeable.

Finally, it's here! Lets have cake!

note: your suppose so stir the reaction for all the 24 hours, but my mag stirrer was K.O, so i shook it every 5 hours, got a little smaller yield but its ok :)

Or, you could have used a small fan with a magnet glued to it, like I suggested. :mad:

Ta daaah:
http://img227.imageshack.us/img227/6459/img0550on1.jpg

Nice, but why not wash it with ice cold ammonium?

Next step is hydrogenation which will be performed as in the paper but with 8% Cu/SiO2
[ http://www.sciencemadness.org/talk/viewthread.php?tid=10704 ],
its nice because its on pyrophoric or pyrogenic catalyst and can be recycled, cheaper then 10% Pd/C, raney nickel or any other. This can open the doors to hydrogenation at atm pressure to the average home chemist :), if Cu/SiO2 doesn't work then 10% Pd/C will be used :(

Cheap, readily available hydrogenation catalyst, you say? *evil grin*

That's shit hot! I may well have a go at that if I can find a sauce for vanillin. It's lazy as hell, but seen as though the reaction appears to be done in aqueous media, if the acetone was of decent quality, distilled, but not dried, there wouldn't be any negative effects on the reaction?

Interestingly enough, there are plenty of other naturally occurring organics, based around benzaldehyde with similar organic groups, I wonder what results would be like if a similar synthesis was done on a different substrate/precursor molecule?

Edit ; does it actually smell like raspberries?
Edit 2 ; Lies and fallacy you fucking cunt! The tags!

Thanks, You could also do it with straight store bought acetone, i doubt it would do much difference (i might as well try it actually). It would work just fine.

Interestingly enough, there are plenty of other naturally occurring organics, based around benzaldehyde with similar organic groups, I wonder what results would be like if a similar synthesis was done on a different substrate/precursor molecule?

Be my guest! New thread tho' :mad: . I was actually looking into it, i will post some of my findings later.

Edit ; does it actually smell like raspberries?[/I]
Edit 2 ; Lies and fallacy you fucking cunt! The tags!

It smells lightly, its kind of nice :) as for the tags, do not hide the evidence :mad: ;)

Klute's been around for time now and is, from what I've seen, reliable, helpful and knowledgeable.

Indeed, he is a very nice person and helped me a lot!

Finally, it's here! Lets have cake!

The caked its a lie :(:mad:



Or, you could have used a small fan with a magnet glued to it, like I suggested. :mad:

Or that son of bitch who is fixing my mag, could speed up :mad:, plus i have no "extra" fans or shit like that :(



Nice, but why not wash it with ice cold ammonium?

Actually, i will try that later today, sounds like a good idea!



Cheap, readily available hydrogenation catalyst, you say? *evil grin*

Oh you...I know wat ur thinking there ;)