Potassium Carbonate → 2-Methyl-6-{4-[1-(2-methoxyphenyl)-1-hydroxypropyl]-phenoxymethyl}-pyridine

Participants

Reaction Steps

7.8 g of α-ethyl-α-(2-methoxyphenyl)-4-hydroxybenzyl-alcohol are dissolved in 65 ml. of methylisobutyl ketone, 9.1 g. of anhydrous potassium carbonate are added, and the reaction mixture is brought up to a boil. Thereafter, a solution of 4.7 g. of 2-methyl-6-chloromethyl-pyridine in 20 ml. of methylisobutyl ketone is added dropwise, and the reaction mixture is slightly boiled for 4 additional hours. After cooling, the reaction mixture is filtered off, and the filtrate is evaporated under reduced pressure. The residue is dissolved in benzene, the solution is washed with a 5% aqueous potassium hydroxide solution and then with water, dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. The crude product is crystallized from a mixture of ethyl acetate and cyclohexane. Melting point: 110° to 111° C.

Provenance & Evidence