Hi!
Swib was looking at the various possibilities for formylating 2-methylhydroquinone, to give 4-methyl-2,5-dihydroxy-BA.
The really good choice would obviously bee the gatterman or the POCl3/DMF formylation, but swib is not thrilled about using either POCl3 or HCN... So, he was looking at some alternate routes for formylations. Here is the routes he is looking at(all the schemes , except the last,are from rhodiums page):
Reimer-Tiemann formylation of 4-Methoxyphenol (Org. React. Vol 28 p16)
Would it be possible to use tolulhydroquinine instead of the 5-methoxyphenol and get the same yeild??
Modification of Vilsmeier-Haack reaction: US Pat
5599988, using oxalylchloride in DMF
Same question as above... and: is it vital to control the temp. ranges as precise as in the patent??
Reimer-Tiemann formylation of 4-Methoxyphenol (Arch. Pharm. 308, p341 (1975))
Basicly the same as the first one, but a little modified. Same questions...
Blazevic and Kolbah: Synthesis;1979;3;161;Hexamethylenetetramine, A Versatile Reagent in Organic Synthesis pp.6
Describes how to formylate using trifluoro aceticacid/HTMA in fair yeilds. How would you suspect this reaction would go given the tolulhydroquinon as a starting material?
Any comments from some fellow bees??
Thanks alot!
Regards
Bandil