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Iodovanillin

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pablos:
http://www.sci.tamucc.edu/pals/morvant/orglab/orglab2/iodinationvanillin.pdf

Easy procedure scalable for the iodination of vanillin.

Captain_America:

pablos:
I would like to discovered this preparation 2 days ago,I have a bunch of shitti bromovanilline and I don´t know what to do with it. All the preparation are to long and I have no inert gas. What can I do with the bromovanilline except hydroxyvanilline?

Rhodium:
Transformation of 5-bromovanillin into syringaldehyde
5-bromovanillin (5 mmol) is refluxed with EtOAc (3 mmol) and CuBr (1 mmol) in 5 M MeONa/MeOH (10 ml) for 14 h; classical work-up leads to pure syringaldehyde (95%).

Reference: https://www.thevespiary.org/rhodium/Rhodium/chemistry/arylhalide.methanolysis.cu-etoac.html

Important details regarding this synthesis are discussed in this thread: Post 275171 (uemura: "Re: Vanillin", Chemistry Discourse)

Inert atmosphere is not required: Post 474077 (Rhodium: "Substituted Vanillins are Resistant to Oxidation", Methods Discourse)

Theroretical discussions:
Post 530151 (Kinetic: "Cu catalysed nucleophilic aromatic substitutions", Methods Discourse)
Post 528896 (Kinetic: "Bromination", Methods Discourse)

Saddam_Hussein:
Do a search for this specific compound on hest's name. He has posted a very simple yet effective method. (MeONa, a dash of CuX and DMF. Shake, boil and recrystallize  ;) )

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