aga
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Competence Advice
As a noob to OC, would i be wasting my time even attempting a synthesis of indole-3-acetic acid as found in this reference :
http://www.orgsyn.org/demo.aspx?prep=CV5P0654
The target compound is indole-3-butyric acid for use as a plant rooting hormone, and the acetic version is the simplest route that i found.
If it could be synthed by such as me, are there any nasties lurking in that process that could leap out and kill someone if it went wrong ?
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Crowfjord
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You have an autoclave? Aside from pressure-related risks, and the fact that indole is really stinky, I don't see any problems with that synthesis.
The procedure looks very simple. As long as you have the proper equipment, you shouldn't have any problems.
[Edited on 24-10-2015 by Crowfjord]
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aga
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Don't have an autoclave yet.
If there is a possibility that i can perform the synthesis, and the figures work out OK then i'll buy one.
Looking to root a LOT of plant cuttings.
Thanks for the advice.
Edit:
Hmm. Do i really know what they mean by 'autoclave' ?
They have always been a high-pressure steam sterilisation device in my understanding.
Is there another chemistry-specific meaning of which i am unaware ?
[Edited on 24-10-2015 by aga]
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zed
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A Parr high pressure reactor is suitable for this reaction. It gets real hot, and there would figure to be many hundreds of pounds of steam pressure
per square inch. In this case, when they say autoclave, they mean....High pressure, stainless steel reaction vessel.
So yeah, without the proper reaction vessel, it would kill you.
I have however, seen papers reporting the formation of such Indole-3-acids, via the refluxing of acetic anhydride and an unsaturated acid/ester.
Like EthylAcrylate, to produce the Indole-3-Butyric acid (or ester).
Indole is not stinky at ordinary temperatures. It has a pleasant floral odor.
Chloroacetic acid might serve to produce Indole acetic acid via an alternate route.
But, if you just want to play with some Indole Butyric acid, you could consider buying some.
Dirt cheap on Ebay. http://www.ebay.com/itm/Indole-3-butyric-acid-99-High-Purity...
Even small quantities are sometimes less than a buck a gram.
Can also be produced via the Fischer Indole Synthesis. 2-Methyl-Indole-3- Acetic acid may be readily produced from Levulinic acid. Sadly, it ain't
much of an auxine.
[Edited on 24-10-2015 by zed]
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aga
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Oh.
Not even properly understanding the name of the equipment is an obvious sign that i should abandon this idea and just buy it instead.
Thanks for the advice.
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battoussai114
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Assuming water vapor to be the main contributor to the pressure inside, you'd be keeping the reactor at around 40 atmospheres for almost one day. High
pressure stainless steel tubing and flanges should withstand more than 100atm, for a loooong time, at the temperature the reactor would be operating.
So it should be possible to build a reactor even if you don't have equipment to machine and weld 304 stainless steel.... Though I wouldn't suggest you
do it.
Batoussai.
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aga
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As much as i'd enjoy DIY-ing a high pressure reactor (which i'm sure i could) the Risk is simply not worth the reward.
Better to attempt that synth after having at least 1 iota of experience (if at all, ever).
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clearly_not_atara
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You could do a coupling between gramine and diethyl oxaloacetate to generate an intermediate which decarboxylates to 4-(indol-3-yl)-2-oxobutyric acid.
Gramine is synthesized at stp and couplings occur via elimination of the methiodide or similar eliminations (ethyl propiolate works well) also at stp.
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blogfast25
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Quote: Originally posted by aga  |
Better to attempt that synth after having at least 1 iota of experience (if at all, ever). |
Also, synths like that should never be undertaken without full knowledge of the Quantum chemistry involved. Well known, that! 
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aga
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... or at least a quantum of knowledge of the chemistry involved ...
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blogfast25
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It would bring solace, yes.
As it happens, the (partial) quantum explanation of the reaction isn't even very hard. 
[Edited on 25-10-2015 by blogfast25]
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UC235
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I think the synthetic route of least resistance to indole-3- acetic acid is probably the Fischer Indole Synthesis and subsequent decarboxylation of
alpha-ketoglutaric acid phenylhydrazone. Still not the easiest prep out there, but workable.
Attachment: ketoglutarateindole.pdf (67kB)
This file has been downloaded 325 times
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ELRIC
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@aga
I know this is not youre target compound, but have you looked into 1-Naphthaleneacetic acid?
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aga
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Sorry. Was i being denser than normal ?
Please be explainings the Quantumings.
| Quote: Originally posted by UC235 | | I think the synthetic route of least resistance to indole-3-acetic acid is probably the Fischer Indole Synthesis and subsequent decarboxylation of
alpha-ketoglutaric acid phenylhydrazone. |
The words used in OC are like alluring magical incantations.
Some words are known : alpha, acid, synthesis, of, the ...
'Decarboxylation' i appear to have Done, yet cannot imagine that it always requires just Heat to work.
keto, glutaric, phenyl and hydrazone are new spells to me.
(maybe phenyl means phenol-shaped-bit-stuck-to-another-bit)
I had not. Have now.
Clearly my whole notion of getting plant cuttings to take root is a vast field of biochemical research and there is far too much to learn in a short
time.
Better to just buy stuff (for now) instead of doing all that fun Learning stuff.
The Responses given here are certainly an Education, that's for sure !
.. and for that i am grateful to You all.
[Edited on 25-10-2015 by aga]
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blogfast25
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By extremely pop...[cough!][Ahem!]...ular demand and because of Manifest Destiny and everthank, I will extend the WM/QM thread and explain it
there, so don't lose the will to live! 
Also, old answers and new questions tonite at 12 hundred UTC, old chap!
[Edited on 25-10-2015 by blogfast25]
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aga
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Excellent. Get over there and start explaining - i'll be waiting.
It would be great to see a specific application of the QM Theory.
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Dr.Bob
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Any reaction that requires that type of heat and pressure is best for after some other ones. I have done a few high pressure reactions, in both glass
pressure tubes and steel parr reactors (also know as autoclaves or "bombs"). They are not cheap, all had multiple safety measures and the most modern
ones are microwave reactors with thick glass vessels, pressure monitoring and high tech temperature control. Still have had problems. But they
can do some neat chemistry in the best of conditions. But they are known as "bombs" for a reason...
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aga
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I agree, hence not being willing to 'just do it'.
The Remote Controlled Lab idea popped up (again) for quite a few moments when considering saying 'what the hell' and just doing it.
Building and using a RemLab<sup>tm</sup> would be very safe at all stages, apart from loading the reagents, and (most
dangerous) visiting it to collect the results.
Edit:
... assuming that the results had not already exited the RemLab<sup>tm</sup> and had arrived via a ballistic mode.
[Edited on 25-10-2015 by aga]
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zed
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Rooting? Try a yogurt maker. Bottom heat.
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aga
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Please explain.
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Little_Ghost_again
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He means try apply heat to the cuttings from the bottom.
Or you could try willow water, it contains many plant hormones. if you look at Ash or willow trees you will see tiny twigs in places that stick out
around parts of the branches and trunk, theses small twigs contain large amounts of growth hormones. Stick in a blender then soak 48 hours in water
and reduce to almost dry.
Dont ask me, I only know enough to be dangerous
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Bot0nist
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At the greenhouse, only the hardest to root cuttings get any hormones. All cutting's trays are placed on tables that have a humidity shade and their
trays sit upon a grid of 1/4 inch PVC through with hot water is circulated from a boiler. Over 80% success for rooted cuttings on average, for
geraniums and various tropicals. So, I concur, bottom heat, and humidity, misting, etc.
[Edited on 27-10-2015 by Bot0nist]
U.T.F.S.E. and learn the joys of autodidacticism!
Don't judge each day only by the harvest you reap, but also by the seeds you sow.
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zed
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Yup! Bottom heat will often do it. Misting can be helpful too. Since, your cuttings have no roots at first, and they transpire H20, to prevent
dessication, it can be important to keep the leaf environment humid. Another trick, is to reduce the number of leaves on your cutting. Some folks go
with one leaf, and cut one half off. Right down the middle.
Perhaps you will find an old waterbed heater, at a garage sale. Don't plug it in, without a body of water over it though. Some models burn right
up, without a heat sink.
Or, you could use the old temporary standby. Place an incandescent lightbulb, inside of an overturned cardboard box. Set your potted cuttings on
top, and monitor the temperature, until you have it adjusted correctly.
Take precautions, to not start a fire.
[Edited on 27-10-2015 by zed]
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