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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: tehanur on April 23, 2009, 05:03:45 PM

Title: 4-acetyl acetanilide synthesis
Post by: tehanur on April 23, 2009, 05:03:45 PM

Hi,

I want to synthesize 4-acetylacetanilide and tried to do a Friedel-Crafts Acylation using Acetanilide and Acetyl Chloride following the synthesis described in a couple of publications and I have tried different conditions, solvents and catalysts but without any success yet.
Any ideas or suggestion of what might went wrong or do you know any alternative reactions?

Thanks.

TBT 

Title: Re: 4-acetyl acetanilide synthesis
Post by: nj_bartel on April 23, 2009, 06:40:30 PM

Details on what you did?

Title: Re: 4-acetyl acetanilide synthesis
Post by: macman104 on April 23, 2009, 07:46:38 PM

Details on what you've tried, and also how do you know it is not working?  Have you characterized any products, that may lead to a better idea of what is going wrong.

Title: Re: 4-acetyl acetanilide synthesis
Post by: tehanur on April 24, 2009, 07:41:03 AM

Here are some additional infos. As mentioned before I tried a FC acyltaion with acetanilide and acetyl chloride using AlCl3 as catalyst and CH2Cl2 (dried) as solvent. The reaction was performed at 60ºC and the reaction times was 24h. I also tried with FeCl3 as catalyst and even adding Zn and ZrO like described in some papers. Different temperatures were tested and THF was tested as different solvent too.

To confirm whether the reaction was successful or not I ran TLCs with the reaction mixture against acetanilide and a 4-acetylacetanilide standard.

Title: Re: 4-acetyl acetanilide synthesis
Post by: AlexB on April 24, 2009, 08:09:43 PM

Complexation of the Lewis acid AlCl3 with acetanilide as well as with acetyl chloride leads to deactivation, often meta substitution and a mess.  See Adv. Synth Catal (ex J. Praktishe Chem) 343 71 (2001) for acetic anhydride Ga(OTf)3 LiClO4 FC reaction on acetanilide.