How to make chlorobenzene

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I am sorry, I thought I saw a document on how to make chlorobenzene around here, but neither of TFSE's seem to have any info.

Referencing "Benzyl Chloride Synthesis by madchemist", it seems one can create chlorine ions in solution with HCl and NaOCl...this may work for toluene, but can they chlorinate a benzene ring?

Anyway, I know this is a bit of a triviality, but I hope someone can find it in their vast wisdom and endless patience to point me to a high-yielding, completely OTC synthesis   (complete with photos, if you please)

Or just some references to chase would be nice too....

[StraightEdge]

I think the reason is that there is little interest in making it. It is not a watched chemical.

Nonetheless, here is what it says in the Merck:
"Produced by the chlorination of benzene in the presence of a catalyst.  Review of manuf, properties, and use:  Faith, Keyes & Clark's Industrial Chemicals, F. A. Lowenheim, M. K. Moran, Eds. (Wiley-Interscience, New York, 4th ed., 1975) pp 258-265."

When you reference a post, you should give the post number inside these characters: [ ]. That way people can see what you are referencing without havign to search for it.

[Mountain_Girl]

Chlorination of benzene

Benzene does not react with chlorine unless a Lewis acid such as ferric chloride is present in the reaction mixture. The reaction is exothermic and the product is the result of substitution rather than addition where chlorobenzene is given in good yield.
           
          FeCl₃         
C₆H₆ + Cl₂ ^__> C₆H₅Cl + HCl
                               
Although the reaction takes place at room temperature, it does not go to completion. The chlorination of benzene is generally carried out at 57°C to ensure 100% conversion.
The introduction of a chlorine atom deactivates the ring somewhat towards further attack. However, this is not sufficient to prevent polyubstitution, and depending on the amount of chlorine present, di-, tri- and higher chlorobenzenes are formed. In order to minimise polysubstitution, excessive temperatures are avoided and the mono product is removed from the reaction zone as soon as it is formed.

Alumina (Al₂O₃) has been used as a catalyst industrially.

References unknown.

Also check:

Patent US3226447

Patent US1946040

Patent BP388818

Patent US2976330

Patent US3636171

Patent US3557227

Patent US2826617

Patent US2943114

Patent US2886605

Patent US2866828

Patent US2949491

Patent US2666085

Patent US2819321

Patent US2920109

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Just like the bromo and iodobenzene sytheses, right? Hah. Should've figured. Well, I'll be getting a copy of the merck soon. Thanks, guys. You're right about just buying the stuff, but I was really hoping to put together a completely otc synthesis that could be large-scaled (unlike RP/I ephedrine). I just wish I could find some otc benzene, cuz that's really the sticking point. This could be considered a "stealth synthesis", because if everything is otc in large quantities, there would be no need to get anything mailed, no need for any front companies, nuthin. Looks good so far.

By the way, thanks for the tip on referencing posts. I was rather wondering about that.