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

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 were charged into a 2 L three-necked flask equipped with a thermometer, a cooling pipe, and a stirrer, followed by stirring at room temperature for 30 minutes. Then, 300 mL of a dimethylformamide solution containing 100 g (412 mmol) of 2-methyl-2-adamantyl chloroacetate was gradually added thereto. The resultant was heated to 40° C., and was then stirred for 4 hours. Following completion of the reaction, 2,000 mL of diethyl ether was added to the reaction mixture, followed by filtration of the resulting mixture. The obtained solution was washed three times with 500 mL of distilled water, followed by crystallization using a mixed solution containing 300 mL of toluene and 200 mL of heptane, thereby obtaining 78 g of an objective compound in the form of a colorless solid (yield: 67%, GC purity: 99%).

1. customequipped with a thermometer
2. additionwas gradually added
3. temperatureThe resultant was heated to 40° C.
4. stirringwas then stirred for 4 hours
5. additionwas added to the reaction mixture
6. filtrationfollowed by filtration of the resulting mixture
7. washThe obtained solution was washed three times with 500 mL of distilled water
8. customfollowed by crystallization
9. additioncontaining 300 mL of toluene and 200 mL of heptane

ORD record

ord-cb6f037f6e0d4508a7afb2f2cd48f6fc

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541157B2