Chloroacetic Acid → (2-Phenylethoxy)acetic acid

Temperature

60 °C

To a stirred mixture of phenethyl alcohol (1.0 g, 8.18 mmol) in DMSO (16 mL) under nitrogen flow, NaH (0.39 g, 16.37 mmol) was added in one portion and the mixture was stirred at 60° C. for 10 min. Following the addition of chloroacetic acid (0.77 g, 8.18 mmol), the reaction mixture was heated at 80° C. for 3 h. The cooled mixture was then poured into H2O and the aqueous phase acidified to pH 1.0 with a 2.0 N HCl solution. The aqueous phase was then extracted with EtOAc (3×20 mL), and the combined organic phase washed with brine and dried over Na2SO4 to afford the title compound (1.11 g, 75%), which was used in the following step without further purification. 1H NMR (DMSO-d6): δ 2.83 (t, J=7.0 Hz, 2H), 3.67 (t, J=7.0 Hz, 2H), 4.00 (s, 2H), 7.15-7.32 (m, 5H), 12.64 (s, 1H).

1. additionwas added in one portion
2. temperaturethe reaction mixture was heated at 80° C. for 3 h
3. extractionThe aqueous phase was then extracted with EtOAc (3×20 mL)
4. washthe combined organic phase washed with brine
5. dry with materialdried over Na2SO4

ORD record

ord-01c5c7980a224801904c49fc7201d7e3

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353075B2