Potassium Carbonate → HCID 11651486, compound

Temperature

75 °C

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.

1. washThe organic layer was washed with water (1.0 L)
2. additionSaturated aqueous solution of sodium bicarbonate (1.2 L) was added to the combined aqueous extracts
3. extractionThe product was extracted from the aqueous phase with two 0.8 L portions of tert-butylmethylether
4. concentrationThe combined organic extracts were concentrated

ORD record

ord-8f9d23c7f40746cdb5c186613477289f

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045652B2