2-(2,4-Bis(1,1-dimethylpropyl)phenoxy)butyryl chloride → 2-(2,4-Bis(tert-pentyl)phenoxy)-N-(3,5-dichloro-4-ethyl-2-hydroxyphenyl)butyramide

Participants

Reaction Conditions

Reaction Steps

A heel was created via batch mode in Reactor 1 by first adding of 16 g (0.16 moles) of potassium bicarbonate, and 55 g of deionized water, and stirring until all of the solid had dissolved. Then, 24 g of isopropanol, 30 g (0.146 moles) of 3,5-dichloro-4-ethyl-2-hydroxyaniline (the amine), 120 g of heptane, and 20 g of toluene were added. The contents of the reactor system were heated to approximately 60° C. while agitating at 400 rpm. To this 2-phase mixture, 57.5 g (0.169 moles) of 2-[2,4-bis(1,1-dimethylpropyl)phenoxy]butyryl chloride (the acid chloride) were added over approximately 45 minutes. The analysis of the upper phase of the mixture was 94% product on a solvent free-basis. The continuous feeds were started at the following rates to provide six hours of residence time: 0.51 g/min 1.36 mmoles/min) of a 55 wt % solution of amine in isopropanol; 1.82 g/min (1.48 mmoles/min) of a solution of the acid chloride solution (27.5 wt % in a mixture of 6 parts of heptane and 1 part of toluene. A 22.5 wt % solution of potassium bicarbonate in water was added to maintain the pH between about 2 and 4. The flowrate of the potassium bicarbonate solution ranged from 0.64-0.68 g/min (1.37-1.46 mmoles/minute).

Provenance & Evidence