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Re: ORGLIST problems with Friedel Craft reaction

From: Alok Shaurya <alokv2.0>
Subject: Re: ORGLIST problems with Friedel Craft reaction
Date: Sun, 26 Jun 2011 14:40:52 +0530
Hi Vedran,

I would not be able to try TiCl4 as my lab does not have it. But I
have made a note of it for future reference.

I tried it with acetic anhydride and it worked well. It gave me a
mixture of mono and di but di a in excess (a lot excess, about 100
times). Also the handling and workup is easier (AlCl3 gives a lot of
mud while workup which is insoluble).
I could not try the microwave though. It requires a special teflon
septum. The lab's student said they had few of them and they are not
re-usable. But my mentor said he could talk the professor to get me at
least one reaction and if successful we can buy some.

Does any one knows how much it costs, those teflon septums for
microwave reactors?

Anyways I will be continuing my project with the acetic anhydride procedure.
Thanks a lot guys for such healthy reponses.


On 6/25/11, Vedran Hasimbegovic <vedran.hasimbegovic> wrote:
> 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,
>
> Vedran
>
> 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.
>>
>


-- 
Alok Shaurya,
Third year Int. MS,
Department of Chemical Science,
IISER Kolkata, WB, India

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