Chloroacetic Acid → HCID 16762791, compound

Temperature

80 °C

A solution of 1-adamantanemethanol (3.11 g, 18.7 mmol) in dry DMF (50 ml) was added to a suspension of sodium hydride (60% dispersion in oil, 1.55 g, 38.6 mmol) in DMF (20 ml). The mixture was warmed to 80° C. for 1 h, cooled to room temperature and a solution of chloroacetic acid (1.86 g, 19.6 mmol) in DMF (25 ml) was added dropwise. The mixture was heated at 80° C. for 17 h. On cooling, the mixture was poured into water (100 ml), extracted with ethyl acetate (2×80 ml), and the extracts were washed with 5%KHSO4 (150 ml), brine (150 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave a white solid which was washed with diethyl ether and water, isolated by filtration and dried in vacuo at 50° C. The product was obtained as a white fluffy solid (1.61 g, 38%). 1H NMR (300 MHz, CDCl3) 4.08 (2H, s), 3.14 (2H, s), 2.00 (3H, br s), 1.70 (6H, q), 1.57 (6H, br s).

1. temperaturecooled to room temperature
2. temperatureThe mixture was heated at 80° C. for 17 h
3. temperatureOn cooling
4. extractionextracted with ethyl acetate (2×80 ml)
5. washthe extracts were washed with 5%KHSO4 (150 ml), brine (150 ml)
6. dry with materialdried (MgSO4)
7. filtrationFiltration and evaporation of the solvent
8. customgave a white solid which
9. washwas washed with diethyl ether and water
10. customisolated by filtration
11. customdried in vacuo at 50° C

ORD record

ord-1d131f9426694eb6b4635877d43db910

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06479531B1