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

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.

1. customA 2 liter 3-neck flask fitted with a thermometer, a cooling tube and a stirrer
2. additionwas added gradually to the reaction mixture
3. temperatureThe temperature was then raised to 40° C.
4. stirringthe reaction mixture was stirred at that temperature for 4 hours
5. additionwas added
6. filtrationthe solution was filtered
7. washthe filtrate was washed 3 times with 500 ml samples of distilled water
8. customCrystallization
9. customyielding 78 g (yield: 67%, GC purity: 99%) of the targeted colorless solid

ORD record

ord-02c337226cd14e5ba2414a3f2e003b3c

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247160B2