Acetonitrile → (Methylthio)methyl hexanoate

In a three-necked 1000 ml. round-bottomed flask fitted with a mechanical stirrer, thermometer and reflux condenser is placed 63.8 g. of hexanoic acid in 200 ml. of acetonitrile. To the stirred mixture is added, at 20°-30° C., 55 g. of triethylamine over a period of 30 minutes. The reaction mixture is stirred at room temperature for an additional 60 minutes. Then is added, at 20°-24° C., 53 g. of chloromethyl methyl sulfide in a few minutes. The reaction mixture is warmed and allowed to reflux for 24 hours. The reaction mixture is cooled to 5°-0° C. and filtered. The solvent is stripped off under vacuum at 12 mm Hg pressure. The residue is taken up in diethyl ether and washed successively with a 10% solution of sodium bicarbonate and with water. The organic layer is dried over anhydrous sodium sulfate. Distillation gives the title ester; b.p. 57°-58° C./2 mm Hg, n20 1.4545.

1. customround-bottomed flask fitted with a mechanical stirrer
2. temperaturethermometer and reflux condenser
3. additionTo the stirred mixture is added, at 20°-30° C.
4. additionThen is added, at 20°-24° C.
5. temperatureThe reaction mixture is warmed
6. temperatureto reflux for 24 hours
7. temperatureThe reaction mixture is cooled to 5°-0° C.
8. filtrationfiltered
9. washwashed successively with a 10% solution of sodium bicarbonate and with water
10. dry with materialThe organic layer is dried over anhydrous sodium sulfate
11. distillationDistillation

ORD record

ord-c68468f6f7a64f8f917bea7a31ca1290

Source dataset

uspto-grants-1983_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04414233