Sciencemadness Discussion Board

Eugenol + HX --> sigh...

Protium - 12-1-2005 at 18:29

Has anybody found an effective and quantitative method of halogenating eugenol's terminal double bond?

thoughts:
1. bubbling HCl through cold ether solution.

2. Bubbling HCl through DMSO OR aqueous DMSO solution.

With HBr

Sandmeyer - 12-1-2005 at 18:53

J. Am. Chem. Soc.; 69; 1947; 1540.

65 percent yield; Indian J. Chem. Sect. B; 27; 1-12; 1988; 308-310.


There is also a Chem Rev paper on DMSO and it's use among other stuff to make ketones from alkenes, if memory serves me. Great paper, a lot of fun chemistry can be done with DMSO. For instance benzaldehydes from benzylchlorides. Nice for chloromethylation freaks...

Mush - 20-9-2017 at 13:45

Quote: Originally posted by Sandmeyer  
J. Am. Chem. Soc.; 69; 1947; 1540.

65 percent yield; Indian J. Chem. Sect. B; 27; 1-12; 1988; 308-310.


There is also a Chem Rev paper on DMSO and it's use among other stuff to make ketones from alkenes, if memory serves me. Great paper, a lot of fun chemistry can be done with DMSO. For instance benzaldehydes from benzylchlorides. Nice for chloromethylation freaks...


Indian J. Chem. Sect. B; 27; 1-12; 1988; 308-310.

Syntheses of ( ± )-Deoxyschizandrin & the Lignan,
l,4-Bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane

A GUNASEKARAN & K BALASUBRAMANIAN*

Attachment: Indian J. Chem. Sect. B; 27; 1-12; 1988; 308-310..pdf (2.8MB)
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[Edited on 20-9-2017 by Mush]