THis is an interesting titbit of info I found whilst surfing google.Dont know how serious it is but.
I recall Dwarfer mentioning using ttt as a chlorinating agent a while back.
Organikum has posted a patent of late, which claims the addition of hexamine avoids ring chlorination.
He also describes a process in which mixtures of benzyl and benzal chloride are treated with aqueous hexamine sollution to yield benzaldehyde.
Once the fucking serch engine is fixed you can look it up for your own.
For those of you that have chlorinated toluene with Cl2, you know how messy
it is. The endpoint is coneviently determined by bp of the solution, but the
HCl that's given off makes for a mess. The fume hood rots, rubber tubing
that conducts the HCl to a trap rots, and the trap has to be carefully
constructed or water will back up into your reaction (shut down and run
time!)!!!! Throughout the reaction, the HCL is pulling benzyl chloride over
into the trap, and hey, it's a mess!
Trichloro triazine trione (TTT) is a cholrinating agent used for swimming
pools and powerful cleansers, the pool type being pressed into 5-7 cm dia
tablets, and available at most US hardware stores. You put a tablet into a
plastic bag and crush it into a powder with a hammer (or squeeze it in a
vise). Put about 300ml of toluene and a large stribar in a 1 liter Erlenmyer
flask on a stir/hotplate. Fit the flask with a short, wide bore, straight,
water cooled condenser and bring the toluene to reflux under stir. Aim a
powerful (150 watt) lamp at the reaction, and add spoonfuls of TTT
cautiously, down through the condenser, watching for a vigorous reaction,
most notably by observing the level where vapors condense in the condenser.
DO NOT OVERFEED THE REACTION. Add a few drops of water (if necessary) to
begin the reaction.
The TTT releases HOCL on contact with water, along with some free Cl2. The
Cl2 reacts at the methyl of the toluene and releases HCl. The HCl goes back
to the TTT and realeases CL2. The beauty of this is that you don't need to
mess with gaseous CL2, and the HCl is recycled! It's cheap, quick, and the
TTT reaction product (cyanuric acid) is easily filtered off from the
finished reaction mixture. Workup consists of simple distillation, after a
quick filtering and water/carbonate wash.
I've only tried this with toluene, but my suspicion is that the in-situ
generation of chlorine will be effective with many substrates. Small scale
experiments, with a few mL in a test tube very conveniently demonstrate the
effect of actinic light on the free radical generation aspect of the
reaction: heat the mixture over a small flame until just at the boiling
point, and expose the test tube to a powerful light. While in the light, the
reaction is vigorous; when the light is turned off, the reaction subsides. A
great demo for the classroom!
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