Sciencemadness Discussion Board

Formylation of Salicylic acid?

guy - 10-6-2007 at 14:35

I know salicylic acid can be formylated with CHCl3 with 20% yield in the ortho form. I need help with the experiment though. How much should I add of NaOH and CHCl3?

kmno4 - 12-6-2007 at 04:31

You can find it in references in Organic Reactions vol.28 (via MadHatter ftp.)

guy - 12-6-2007 at 12:46

How do you guys get access to ftp's?

PainKilla - 12-6-2007 at 13:04

This is relevant:

The Reimer-Tiemann Reaction.
Hans Wynberg
pp 169 - 184; DOI: 10.1021/cr60204a003

Attachment: reimer.pdf (1.4MB)
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guy - 12-6-2007 at 13:15

Thanks, according to that I should use at least a 10:1 NaOH to phenol molar ratio :o
I could do that but it says I need to separate using steam distillation which is out of the question for me. I guess bisulfite would work though.