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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: maverick1996 on April 04, 2016, 03:58:54 AM

Title: Will this work? - Organic Synthesis
Post by: maverick1996 on April 04, 2016, 03:58:54 AM

Hey guys!!

I am just wondering whether this method would work? And if there is a better way of doing it?

I have attached both the question and my scheme

Thank you

Title: Re: Will this work? - Organic Synthesis
Post by: AWK on April 04, 2016, 04:07:41 AM

Wrong position of double bond in last two lines.

Title: Re: Will this work? - Organic Synthesis
Post by: maverick1996 on April 04, 2016, 04:15:21 AM

Thank you

Title: Re: Will this work? - Organic Synthesis
Post by: Alwin Kristen on April 04, 2016, 06:22:37 AM

How would you know that your methyl iodide reacts with lactaldehyde and not with NaOH? Could another base be better? Some big and just strong enought to remove proton from hydroxyl group?

Title: Re: Will this work? - Organic Synthesis
Post by: AWK on April 04, 2016, 06:48:18 AM

Good remark. Aldehyde also reacts itself in presence of NaOH. Though conditions are theoretically anhydrous. I used CaH₂ or molecular sieves for drying DMSO.

Title: Re: Will this work? - Organic Synthesis
Post by: kriggy on April 04, 2016, 09:32:58 AM

You could probably get rid of the hydroxy group by use of HI in one step.

Im wondering, if acetone derivative could be used in this, like forming enol-ether and then arylate it with bromobenzene in presence of some metal catalyst

Title: Re: Will this work? - Organic Synthesis
Post by: clarkstill on April 04, 2016, 11:07:46 AM

Any way you could think of using an epoxide?

Title: Re: Will this work? - Organic Synthesis
Post by: discodermolide on April 04, 2016, 12:45:04 PM

What about a metal catalysed aryl-vinyl cross coupling?

Title: Re: Will this work? - Organic Synthesis
Post by: maverick1996 on April 06, 2016, 02:58:24 AM

Thank you all for your input, I'm a first year so I'm just going by the reactions that I've already seen but I'll give it a shot with the ways that you have suggested :)

And about using NaOH - thank you

Title: Re: Will this work? - Organic Synthesis
Post by: subro on April 10, 2016, 06:17:30 AM

Quote from: clarkstill on April 04, 2016, 11:07:46 AM

Any way you could think of using an epoxide?

Yeah, I was going to post this.

Title: Re: Will this work? - Organic Synthesis
Post by: phth on April 10, 2016, 08:35:22 PM

Quote from: discodermolide on April 04, 2016, 12:45:04 PM

What about a metal catalysed aryl-vinyl cross coupling?

+1 this transformation can be done in 1 step. Ni(II) Hiyama coupling.  Ni is better than Pd.