Potassium Carbonate → 2-(2-Ethyl-5-methoxyphenoxy)-N,N-dimethylethanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-ethyl-5-methoxy-phenol (103.8 g, 682 mmol) in tetrahydrofuran (490 mL) was added a mixture of potassium hydroxide (75.8 g, 887 mmol), potassium carbonate (235.7 g, 1.71 mol, powder form), and 1-chloro-2-dimethylamino-ethane hydrochloride (98.2 g, 682 mmol) followed by addition of toluene (1.10 L). The mixture was stirred at 75° C. for 28 hours. The reaction mixture was poured into ice-cold water (1.0 L). The organic layer was washed with water (1.0 L) and then twice with 1L of 1 M HCl. Saturated aqueous solution of sodium bicarbonate (1.2 L) was added to the combined aqueous extracts, the pH was adjusted to 11 with 30% sodium hydroxide solution (220 mL). The product was extracted from the aqueous phase with two 0.8 L portions of tert-butylmethylether. The combined organic extracts were concentrated to give 144.2 g (91% yield) of [2-(2-ethyl-5-methoxy-phenoxy)-ethyl]-dimethyl-amine as a yellow oil.

Provenance & Evidence