29515-39-7Relevant articles and documents
Concurrent synthesis of vanillin and isovanillin
Huang, Wei-Bin,Du, Cai-Yan,Jiang, Jian-An,Ji, Ya-Fei
, p. 2849 - 2856 (2013/07/26)
A method for concurrent synthesis of vanillin and isovanillin has been developed by a nonregioselective Vilsmeier-Haack reaction of O-alkyl guaiacols. O-Alkylation of guaiacol provided the corresponding O-alkyl guaiacol (1), which was then formylated with N-methylformanilide/phosphorus oxychloride to give a mixture of 4-alkoxy-3-methoxy-benzaldehyde (2) and 3-alkoxy-4- methoxybenzaldehyde (3). Finally, the obtained mixture underwent a selective dealkylation by anhydrous aluminium trichloride, while leaving methyl groups intact to simultaneously achieve the significant fine chemicals vanillin and isovanillin.
Palladium charcoal-catalyzed deprotection of O-allylphenols
Ishizaki, Miyuki,Yamada, Makoto,Watanabe, Shin-Ichi,Hoshino, Osamu,Nishitani, Kiyoshi,Hayashida, Maiko,Tanaka, Atsuko,Hara, Hiroshi
, p. 7973 - 7981 (2007/10/03)
Allyl aryl ethers can be easily cleaved by the use of 10% Pd/C under mild and basic conditions. The present reaction would involve a SET process rather than a π-allyl-palladium complex. The scope and limitation of this new deprotective methodology is also described.
Radical isomerization via intramolecular ipso substitution of aryl ethers: Aryl translocation from oxygen to carbon
Lee, Eun,Lee, Chulbom,Tae, Jin Sung,Whang, Ho Sung,Li, Kap Sok
, p. 2343 - 2346 (2007/10/02)
Bromopropyl aryl ethers an converted to 3-arylpropanols under standard radical generating conditions in the presence of tributylstannane and AIBN. This rearrangement involves intramolecular ipso attack of the alkyl radicals which generates spiro cyclohexadienyl radical intermediates.
