2-Chloroethanol → 2-(2-Chloroethoxy)-2-methylpropanenitrile

温度

60 °C

(Navalokina, R. Et al J. Org. Chem. USSR (Engl. Trans.), 1980, 16, 1382–1386.2) Ramalingam, K. U.S. Pat. No. 4,864,051, 1989.). A 250 mL round bottom flask was charged with ZnCl2 (68.14 g, 0.5 mole) which was then fused by heating under vacuum. After returning to room temperature the material was placed under an atmosphere of N2. To this was added acetone cyanohydrin (45.66 mL, 0.5 mole) followed by 2-chloroethanol (50.24 mL, 0.75 mole) and the mixture placed in a preheated oil bath (60° C.). After stirring for 18–20 h at 60° C., the reaction mixture was cooled, diluted with water (300 mL) and washed with CH2Cl2 (5×100 mL). The combined CH2Cl2 extracts were dried (Na2SO4), filtered and concentrated under vacuum to afford the crude product as a yellow liquid. Purification was accomplished by vacuum distillation (10 mm Hg) using a vigreux column. The fraction boiling between 65–75° C. was collected to afford the desired product as a colorless oil (47.1 g, 63.8% yield). 1H NMR (500 MHz, CDCl3) δ ppm: 3.85 (2H, t, J=5.8 Hz), 3.64 (2H, t, J=5.8 Hz), 1.60 (6H, s).

1. temperatureby heating under vacuum
2. customAfter returning to room temperature
3. customthe mixture placed in a preheated oil bath
4. custom(60° C.)
5. temperaturethe reaction mixture was cooled
6. washwashed with CH2Cl2 (5×100 mL)
7. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customto afford the crude product as a yellow liquid
11. customPurification
12. distillationwas accomplished by vacuum distillation (10 mm Hg)
13. customboiling between 65–75° C.
14. customwas collected

ORDレコード

ord-76d197829d434f49a41f19db4306f449

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07176196B2