The Vespiary

The Hive => Novel Discourse => Topic started by: psycosmo on August 03, 2001, 11:42:00 AM

Title: Cyclization to phenethylamines
Post by: psycosmo on August 03, 2001, 11:42:00 AM

I've been trying to find info on cyclizing substituted alkenes to their corresponding benzene compounds without much success. Is this possible? Could one say, cyclize a 1,2,3-trimethoxy 5-ethylamino hexene/hexane into mescaline, or a similar reaction for any other phenethylamine. I kmow its 2 EZ to be true but it seemed so potetially elegent I just had to post it....

Title: Re: Cyclization to phenethylamines
Post by: b159510 on August 03, 2001, 11:46:00 AM

Too easy? That would be a major pain.

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Title: Re: Cyclization to phenethylamines
Post by: Lilienthal on August 03, 2001, 07:05:00 PM

There is that nice cyclization / aromatization reaction to olivetol (analogs) starting from nonenone. I will post the ref later.

Title: Re: Cyclization to phenethylamines
Post by: Osmium on August 03, 2001, 08:14:00 PM

acetone + hexanal ---[aq. NaOH]---> 3-nonen-2-one 47% [1]

3-nonen-2-one + dimethylmalonate ---[NaOMe]---> complicated intermediate 70% [2]

complicated intermediate ---DMF, Br2, heat---> olivetol 85% [3]

[1] J. Gen. Chem. USSR 33, 134 (1963)
[2, 3] J. Org. Chem. 42, 3456 (1977)

best olivetol synth I know so far. Cheap, easy, yields ok. Starting with another aldehyde will yield olivetol analogs.