3580-76-5Relevant academic research and scientific papers
Synthesis of Phenolic Ketones, an Ester Ketone of Guaiacol, and a Ketone of Veratrole Containing Chlorine, Bromine, or Iodine in the Side-chain
Kossmehl, Gerhard,Frohberg, Hans-Christian
, p. 50 - 64 (2007/10/02)
The ω-bromo and ω-chloro ketones 1-8, 10-14 of phenols as well as the ω-bromo ketone 9 of veratrole are synthesized according to the Friedel-Crafts acylation (FCA) using different variations and specific reaction conditions.Under these conditions hydroquinone furnishes the esters of the ω-bromo- and ω-chlorocarboxylic acids 28-31, whereas phloroglucinol does not result in defined reaction products.Guaiacol yields 16 with an ester as well as a ketone group at its aromatic nucleus.Bromination of 3',4'-dihydroxyisobutyrophenone with CuBr2 leads to 2-bromo-3',4'-dihydroxyisobutyrophenone (15).The ω-iodo ketones 17-27 of phenols and their methyl ethers have been obtained from the corresponding ω-bromo or ω-chloro ketone on treatment with NaI in acetone.
