Reference request

this one?... UTFSE, google to be precise....

PS It ain't a flame, but try it out - I personally spend a shitload of time on it, multi keyword searches, site specific searches, allinurl:, site: etc. It is amazing how much is out there if you look.



[Edited on 9-8-2010 by un0me2]

Attachment: Taber.Patel.Hambleton.Vanillin.Synthesis.from.4.Hydroxybenzaldehyde.pdf (168kB)
This file has been downloaded 1496 times

Appreciate you pointing the pdf out to me, actually I do UTFSE a lot but I couldn't find that one.

Glad you weren't flaming me, I'd have had to use my CO2 extinguisher on ya

The link gsd pointed me to lead me to:

"You are not authorised to view this forum"

hence my reply to him.

Ummmm, it has the experimental procedure in the latter part of the 14 part file (the description thereof is at the start).

Running the reaction:

To the Br2-MeOH mixture in vial A, add 100 mg (0.82 mmol) of 4-hydroxybenzaldehyde,cap the vial and shake in ice-water bath for 30 seconds. Remove the caps of both vials and pour the contents of vial A into the already-hot contents of vial B (Note 2). Replace the cap with the syringe barrel on vial B and heat this mixture in the 130 oC silicon oil bath in a fume hood for one hour. During this time, prepare a flash chromatography column using 5.0 g of flash silica gel. You should also prepare the solvent to be used in the column by combining 30 mL of Et2O and 170 mL of petroleum ether in a 250 mL Erlynmeyer flask.

By the end of the hour, most of the solvent that was in vial B will have collected in the syringe barrel and a dark brown residue will remain in vial B. Remove vial B from the heat source and let it stand until it is cool. Do not burn yourself! Remove the cap from vial B. Using a total of 6 mL of 3.0 M aqueous HCl and gently scraping the solid using a spatula, transfer the contents of vial B to a separatory funnel. Extract with 3x 5 mL EtOAc, (a small separatory funnel or a centrifuge tube and a pipette may be used), combine the organic extracts and dry with Na2SO4. Transfer the supernatant to a round-bottom flask, add 0.5 g silica gel and place the flask on a rotary
evaporator to remove excess solvent, leaving a dry light brown powder.

It then proceeds to deal with the preparation of a column and the subsequent chromatographic separation of the components. I wouldn't say that was a "tease" as such...