20675-21-2Relevant academic research and scientific papers
Reaction of α-(n-alkylcarbonyloxy)alkyl (ACOA) halides with 4-hydroxyacetanilide and 2,2,5,7,8-pentamethyl-6-chromanol: The effect of steric hindrance on reaction path
Thomas, Joshua D.,Sloan, Kenneth B.
, p. 272 - 278 (2008/12/22)
A convenient synthesis of α-(n-alkylcarbonyloxy)alkyl (ACOA) iodides has been developed and a homologous series of n-alkylcarbonyloxymethyl (ACOM) iodides have been used to alkylate 4-hydroxyacetanilide (acetaminophen, APAP), a sterically unhindered phenol, and a sterically hindered phenol (2,2,5,7,8-pentamethyl-6-chromanol). Steric hindrance was not a significant factor in the ratio of acylated (Path b) to alkylated (Path a) for these reactions. Given the reported toxicity associated with sterically hindered ACOM prodrugs, n-alkyl ACOM and ACOA promoieties present themselves as viable alternatives to the more commonly used pivalate-based derivatives. Georg Thieme Verlag Stuttgart.
