2-Chloroethanol → HCID 55302949, compound

Temperature

90 °C

Zinc chloride (36.03 g, 264 mmol) was fused using a propane torch while under vacuum. The molten salt was cooled and the evacuated flask was flushed with nitrogen. The flask was loaded with 1-hydroxycyclobutanecarbonitrile (15.10 g,) and 2-chloroethanol (17.7 g, 218 mmol) and stirred with heating (90° C.) for 20 hours. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (1×150 mL, 4×100 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated to an oil in-vacuo. The crude product was purified by vacuum distillation (b.p.12 85° C.) to give title compound (5.00 g, 31.3 mmol, 16.4% over two steps) as a clear liquid. 1H NMR (500 MHz, CDCl3) δ: 3.75 (2H, t, J=5.5 Hz), 3.65 (2H, t, J=5.6 Hz), 2.52-2.61 (2H, m), 2.31-2.43 (2H, m), 1.91-2.06 (2H, m).

1. temperatureThe molten salt was cooled
2. customthe evacuated flask was flushed with nitrogen
3. extractionextracted with ethyl acetate (1×150 mL, 4×100 mL)
4. dry with materialThe combined organic layers were dried (sodium sulfate)
5. filtrationfiltered
6. concentrationconcentrated to an oil in-vacuo
7. distillationThe crude product was purified by vacuum distillation (b.p.12 85° C.)

ORD record

ord-b52d0a5cbbc8459d8f6c1e647e977df5

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07893055B2