2-Chloroethanol → HCID 21069785, compound

Temperature

60 °C

Zinc chloride (68.1 g, 0.5 mol) was fused under vacuum as described in the procedure for the synthesis of intermediate 23. The molten zinc was cooled and the evacuated flask was flushed with nitrogen. The flask was loaded with intermediate 28, 2-ethyl-2-hydroxybutanenitrile, (40.3 g, 0.5 mol) and 2-chloroethanol (50.5 mL, 0.75 mmol) then stirred at 60° C. for 20 hours. The reaction mixture was diluted with water (250 mL) and extracted with dichloromethane (1×250 mL, 4×100 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated in-vacuo. The crude product was purified by vacuum distillation (bp 83° C., 10 mmHg) to give the title compound (52 g) containing unreacted intermediate 28. 1H NMR (500 MHz, CDCl3) δ ppm: 3.82 (2H, t, J=5.8 Hz), 3.64 (2H, t, J=5.8 Hz), 1.83 (4H, J=7.3 Hz), 1.03 (6H, t, J=7.6 Hz).

1. customthe evacuated flask was flushed with nitrogen
2. extractionextracted with dichloromethane (1×250 mL, 4×100 mL)
3. dry with materialThe combined organic layers were dried (sodium sulfate)
4. filtrationfiltered
5. concentrationconcentrated in-vacuo
6. distillationThe crude product was purified by vacuum distillation (bp 83° C., 10 mmHg)

ORD record

ord-21e9210a5aa14a428a53ba985cb2f9c9

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176196B2