Potassium Iodide → Methyl 4-[5-(4-cyanophenoxy)-pentoxy]-3-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-5-chloropentane (3794 g, 20.45 mol) in acetonitrile (38 L) is added 4-cyanophenol (2437 g, 20.45 mol) and powdered powdered potassium carbonate (2827 g, 20.45 mol). This suspension is heated with stirring under nitrogen at 96° C. bath temperature (82° C.-internal) for 20 hours. Additional powdered potassium carbonate (2827 g, 20.45 mol.) is then added to the hot reaction mixture followed by potassium iodide (3397 g, 20.45 mol) and methyl vanillate (3725 g, 20.45 mol). The reaction mixture is heated under nitrogen for another 3 days until TLC shows no intermediate chloro compound present. The bath is removed and stirring stopped. The reaction mixture is filtered hot through a filter crock and into another 20 gallon reactor. The filtrate is stirred and cooled with an ice bath to 10° C. for 3 hours and the product filtered, washed with diethyl ether (4×1 L) and dried in vacuo (50° C., 3 mm Hg) to give methyl 4-[5-(4-cyanophenoxy)-pentoxy]-3-methoxybenzoate, mp 105°-107° C., HPLC indicating a purity of 99.8%.

Provenance & Evidence