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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: blekinva on December 06, 2008, 07:52:30 PM

Title: HELP (4,4) dimethanol cyclohexene synthesis?
Post by: blekinva on December 06, 2008, 07:52:30 PM

Please help me figure out what reagents to use to synthesise this compound:

it is a hexene ring (one double bond) and I have to have two methanol groups attached at the same (i.e. the 4) position

Title: Re: HELP (4,4) dimethanol cyclohexene synthesis?
Post by: agrobert on December 06, 2008, 08:34:31 PM

http://en.wikipedia.org/wiki/Diels-Alder_reaction

What is the mechanism?

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Title: Re: HELP (4,4) dimethanol cyclohexene synthesis?
Post by: refid on December 06, 2008, 08:38:37 PM

Oh yeah, for got about Diels Alders .

Would it be possible to use cyclohexenone and LDA/CH3Br and filter out the side products?

Title: Re: HELP (4,4) dimethanol cyclohexene synthesis?
Post by: blekinva on December 06, 2008, 09:02:38 PM

diels-alder....perfect

and it doesnt need any other reagent or work up to carry out does it?

hence, i would just mix (1,2) propa-di-ene and chloroethene?

thank you SO much for this help

Title: Re: HELP (4,4) dimethanol cyclohexene synthesis?
Post by: blekinva on December 06, 2008, 09:07:47 PM

correction... buta-1,3-diene