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Re: ORGLIST problems with Friedel Craft reaction

From: Vedran Hasimbegovic <vedran.hasimbegovic>
Subject: Re: ORGLIST problems with Friedel Craft reaction
Date: Sat, 25 Jun 2011 02:30:52 +0200
Hi Alok,

Try titanium(IV) chloride (TiCl4) if you have some. I’ve never
acylated ferrocene but I generally use TiCl4 for acid chloride-based
Fridel-Crafts acylations and it works like a charm.

All the best,


On 6/24/11, Alok Shaurya <alokv2.0> wrote:
> Dear all,
> Thank you for your replies.
> Graham, I think you have a valid point. Last succesful experiment was a
> month ago, when it was summer at its full. Now that monsoons have hit India,
> and I am at the edge of Bay of Bengal, which was under a cyclone just days
> ago, the humidity in air sure must have increased. This must degrade the
> AlCl3 much faster (Its an old bottle too). Also the AlCl3 I have is not
> completely like a powder. It has lumps (small though). I checked wikipedia
> and I saw that pure AlCl3 is white while mine has greenish tinge. I take it
> that it has absorbed lot of moisture. DCM, that I am, using was dried with
> CaH overnight and distilled so I doubt that there is problem there, but I
> will check it too.
> Dr. Ismail, sublimation might not be possible for me right now (It was my
> first clue too). Although I want to do it (I have never done sublimation),
> but since AlCl3 is corrosive, PhD students in my lab are not for it (I am
> just a third year int. master students). We have ordered fresh AlCl3. But
> your last reference is really cool. There is a microwave in a lab I know.
> Its fast (only 5 mins :D) and seems simple. I will give it a try. I want to
> synthesize 1,1`-diacetyl ferrocene. I guess I will increase the
> concentration of phosphoric acid. I will update the results.
> Thank you all once again.

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