2-Chloroethanol → 2-tert-Butyl-4-(2-hydroxyethoxy)phenol

Participants

Reaction Conditions

Reaction Steps

332 g (2 mol) of t-butylhydroquinone and 1 g of potassium iodide were dissolved in 2 l of water under nitrogen atmosphere, and were heated to 80° C. Thereafter, to the solution thus obtained, were dropwise added 232 g (2.8 mol) of 48% sodium hydroxide aqueous solution and 200 g (2.5 mol) of ethylene chlorohydrine at the same time for 3 hours while constantly maintaining alkaline. After finishing this dropwise addition, the resultant reaction mixture was heated for 8 hours at the reflux temperature. After cooling the reaction mixture thus obtained, the reaction mixture was neutralized with sulfuric acid and was extracted with toluene. After removing solvent, the remaining material was distilled under reduced pressure and the distillate was recrystallized from toluene to obtain 200 g of 2-t-butyl-4-(2'-hydroxyethoxy)phenol. The reaction formula (alkylation) is illustrated in the following. ##STR4##

Provenance & Evidence