Sodium Bicarbonate → 2-(4-hydroxybutyloxy)acetic Acid Tert-Butyl Ester

Participants

Reaction Steps

To a solution of 36.21 g of 2-[4-(2-tetrahydropyranyloxy)butyloxy]acetic acid tert-butyl ester in 360 ml of methanol, 47.77 g of p-toluenesulfonic acid monohydrate was added. After stirring at room temperature for 30 minutes, the reaction solution was neutralized with an aqueous sodium hydrogen carbonate solution and the solvent was evaporated under reduced pressure. The residue was diluted with water, extracted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 17.02 g of the desired compound as a colorless oily substance.

Provenance & Evidence