If one were to use water to hydrolyse aspirin and make salicylic acid, could one then use HI + P to reduce the two OH groups on salicylic acid and
make benzaldehyde?
If not that then the only other way I can think of is to use PI3 to convert the OH to I and then LiAlH4... but that will also reduce the ketone which
you'll have to oxidize back...
[Edited on 23-8-2009 by kerousel]turd - 23-8-2009 at 14:36
No. Neither the phenol group, nor the carboxylic acid group are aliphatic alcohols. Check a basic organic chemistry text.
PS: beginnings was the right place for this question.kerousel - 23-8-2009 at 14:47
I wasn't sure about the one on the benzene ring, but I'm pretty sure that the OH on the carboxyl will reduce... if not with HI + P, then by converting
to R-I with PI3 and following with lithium al hydride... I've seen it in many places examples of this.
[Edited on 23-8-2009 by kerousel]kclo4 - 23-8-2009 at 15:51
There are better ways to produce benzaldehyde.
Going via aspirin, if it is possible at all, is absolutely not worth it.
Look up the manganese persulfate oxidation, there are a couple of those threads floating around, one being the toluene -> benzaldehyde thread. kerousel - 23-8-2009 at 18:46
Oh ok then, just seemed like it would be easy, plus I've got aspirin, idk where to get toulene... well I guess you can still get phenol from
aspirin...
I still think it's doable though... like ok phenol + phosphorous pentachloride makes phenyl chloride- so that OH is replaceable with halogens, just
like the OH on the carboxyl should be... LiAlH4 should replace the halogens with hydrogens (although it would probably also reduce the ketone to OH so
you'll have to oxidize it back with KMnO4 or something)
I just thought you could skip the LiAlH4 and KMnO4 by using HI + P instead...kclo4 - 23-8-2009 at 19:13
How is it you can get LiAlH4, KMnO4, PCl5, HI and P but not know where to get toluene?
Jesus.. you are in one crazy country lol
Toluene can be had at most stores, especially home and garden stores or at least online. Its only 10-15 dollars a gallon. A lot cheaper then aspirin
per mole.
KMnO4 generally oxidizes all the way too carboxylic acid so that won't work.
COOH, is a completely different functional group then is OH, The "OH" on the carboxyl doesn't act at all like the OH of phenol or other alcohols at
all to my understanding. Also the carbonyl in the carboxyl doesn't act at all like an aldehyde, or a ketone.
Benzaldehyde from aspirin is crazy.
[Edited on 24-8-2009 by kclo4]kerousel - 23-8-2009 at 19:51
oh, ok lol. Guess I still have quite to learn. Wait do they sell toulene like next to acetone at household stores? Will have to pay a visit there
then. Ah I can't remember, I can almost imagine an acetone-like tin can saying "toulene" on it. Although I thought it was like a drug precursor or
something so hard to get...
And no unfortunately I don't have LiAlH4 or KMnO4, I only have HI, I2, P and PI3. But I wouldn't have went through that amount of trouble with hydride
and permanganate anyways, I thought it would be doable with just HI + P. Oh well. Thanks.
Edit: btw, If I do find toulene, do you know if ammonium or sodium persulfate can be used instead of manganese persulfate? Because an electronics
store near by sells 1kg bottles of it as crystal powder. I bought it once, it makes paper burn very energetically! drop a piece of steel in a water
solution of it, and the steel will dissapear into a reddish brownish green solution!
[Edited on 24-8-2009 by kerousel]kclo4 - 23-8-2009 at 20:05
Yessir its by the other solvents generally speaking.
Various persulfates work, it seems this site and the the vespiary is getting to be riddled with manganese persulfate threads, as well as the manganese
ammonium alum, possible other persulfates such as manganese sodium persulfate, etc.
Recently I did a little electrolysis of an unpartitioned cell of NaHSO4 and MnSO4 and it turned into a dark red/brown color that can oxidize alcohols,
and even chlorides to produce chlorine! both the electrodes were graphite. I only did this for about then minutes though.. so I produced very little.
It appeared MnO2 formed on one of the graphite rods, but I cannot be sure.
.. anyways my point is go look for the threads
Cuauhtemoc - 23-8-2009 at 20:12
Toluene is not a drug precursor, but it can obviously be used by "cookers" as a solvent to get ephedrine from pills.
KMnO4 is also easy to get, I think you can buy it at any drugstore.not_important - 23-8-2009 at 20:14
Also in the old threads is the conversion of styrene to benzaldehyde, and styrene can be had in decent yield by heating scrape polystyrene -
resin/recycling code #6 or PS.
kerousel - 23-8-2009 at 20:19
Alright KClO4, you're right I'll definitely have to do some more research into this...
[Edited on 24-8-2009 by kerousel]Siddy - 23-8-2009 at 20:36
Real reason for toluene taken off the shelves across europe and in many other countries it that its been moved up a level on the teratogen scale.kerousel - 24-8-2009 at 11:34
Also in the old threads is the conversion of styrene to benzaldehyde, and styrene can be had in decent yield by heating scrape polystyrene -
resin/recycling code #6 or PS.
I found another way of polystyrene>styrene first hand today- was carrying a bit of gasoline in a styrofoam cup, when suddenly the lower half of it
falls through right onto my floor... after the gasoline evaporated there was a very sticky residue left kclo4 - 24-8-2009 at 12:46
The gas only dissolved the polystyrene, it did not depolymerize it.
If it is sticky it is likely not all of the gasoline has evaporated.
If you find the link to the styrene to benzaldehyde thread I'd be interested in looking at it. Is it at all practical? kerousel - 24-8-2009 at 13:53
oh yeah you're right it's not sticky anymore- just like a semi-hard resin.
after some google searches, i think the easiest styrene to benzaldehyde is "H2O2 + formic acid". all the other one's i've seen require strange metal
oxide catalysts, etc.
[Edited on 24-8-2009 by kerousel]kclo4 - 24-8-2009 at 14:11
Yeah, neither seem very appealing. H2O2 and formic acid aren't the most OTC thing in the world, and that is after you make the styrene from the PS. entropy51 - 24-8-2009 at 14:46
Yeah, neither seem very appealing. H2O2 and formic acid aren't the most OTC thing in the world, and that is after you make the styrene from the PS.
30% H2O2 is OTC as wood bleach at the hardware store.
HCOOH is easily made from oxalic acid and glycerin. Both are OTC, oxalic acid as, once again wood bleach at the hardware store. In some places HCOOH
is OTC as scale remover.Sedit - 24-8-2009 at 14:48
Even farther off topic Styrene monomer is over the counter(body resin) as is formic acid(wood stripper) and 35% hydrogen peroxide as well. If the
process produces good yeilds given the avalibility of Benzaldahyde I would think its worth it.kclo4 - 24-8-2009 at 14:51
Interesting, I've been unable to locate oxalic acid or H2O2 under any circumstances where I am located. Well, besides the oxalic acid in bar keepers
friend which is a pain for me to extract when I have other things to do.
I didn't know about the H2O2 as a wood bleach. I'll have to keep my eyes open, same goes for the HCOOH as a scale remover. What do mean by scale? entropy51 - 24-8-2009 at 14:57
I think it's scale in tea kettles, from calcium deposits from hard water. But I haven't seen that product here. But the hardware store has pure
(tech grade, no additives) oxalic and 35% H2O2.Magpie - 24-8-2009 at 15:08
Other places to look:
oxalic acid: paint store
35% H2O2: helath food storekclo4 - 24-8-2009 at 15:09
Thank you very much!
Why on earth would 35% H2O2 be in a health food store?kerousel - 24-8-2009 at 15:32
Well if you don't find it, you can always dissolve oxi-clean (sodium percarbonate) in hot water to make like 20% h2o2. If you add hcl to it that could
make it higher yet by reducing carbonate ions...
[Edited on 25-8-2009 by kerousel]Magpie - 24-8-2009 at 15:48
Quote:
Why on earth would 35% H2O2 be in a health food store?
I've been told it is used for sterilizing hydroponics equipment.
The oxalic acid is used as a wood bleach.Sedit - 24-8-2009 at 16:20
To answer that quote, the stuff I get from the healthfood store is used as a safe alternative to NaOCl and bromine tabs for cleaning spas and
hottubes. I use it all the time around the house instead of using bleach because I think it works better and don't stink to all hell.entropy51 - 24-8-2009 at 16:45
you see what he did siddy? Post a bunch of useless links to keep you from asking anything else, without actually getting you anywhere.kclo4 - 28-8-2009 at 02:06
What the hell kerousel?!
Look at what siddy asked! he wanted the link to the thread on styrene to benzaldehyde.
He gave multiple threads addressing the topic, and even pointed out individual posts. You would have noticed that if you had taken the time to read
what siddy posted, and what the links were!
The links are hardly useless, and to call them useless is not an insult to him but an insult to the members who posted in the threads he has linked to
who have researched and shared their knowledge for everyone to see.
Kerousel, what was the point you were trying to make anyways? kerousel - 28-8-2009 at 03:27
Oh no, what I meant was that I didn't feel like reading them. Sorry if I insulted not_important, he's been quite helpful in some of my past lives.
You're quite helpful too kclo4.
