Glycolic Acid → 2-(2-(2-Methyl-2-adamantyloxy)-2-oxoethoxy)-2-oxoethanol

Participants

Reaction Steps

A 2 liter 3-neck flask fitted with a thermometer, a cooling tube and a stirrer was charged with 37.6 g (494 mmol) of glycolic acid, 700 ml of DMF, 86.5 g (626 mmol) of potassium carbonate and 28.3 g (170 mmol) of potassium iodide, and the resulting mixture was stirred for 30 minutes at room temperature. Subsequently, 300 ml of a dimethylformamide solution containing 100 g (412 mmol) of 2-methyl-2-adamantyl chloroacetate was added gradually to the reaction mixture. The temperature was then raised to 40° C., and the reaction mixture was stirred at that temperature for 4 hours. Following completion of the reaction, 2,000 ml of diethyl ether was added, the solution was filtered, and the filtrate was washed 3 times with 500 ml samples of distilled water. Crystallization was then performed using a mixed solution of toluene (300 ml) and heptane (200 ml), yielding 78 g (yield: 67%, GC purity: 99%) of the targeted colorless solid.

Provenance & Evidence