1158-20-9Relevant articles and documents
Selective acylation of phenols in boron trifluoride diethyl etherate solution and the mechanistic implication
Xiao, Zhu-Ping,Wei, Wei,Huang, Shen,Lin, Xiao-Yi,Peng, Bin,Wang, Xu-Dong,Zhang, Lei
, p. 8039 - 8042 (2015/02/02)
In the presence of boron trifluoride diethyl etherate (BF3 · OEt2), direct acylation of phenols with free carboxylic acid is chemoselective and regioselective and no demethylation, if any, was observed. The para-directing effect of BF3·OEt2 is attributed to the large steric hindrance of the boron trifluoride-phenolic hydroxyl group complex, which blocks the ortho-acylation from occurrence. Microwave irradiation could not change the regioselectivity of BF3·OEt2 except the reaction time being greatly shortened.