Dimethyl Sulfate → Methyl 2-ethylbutyrate

A mixture of 116 g (1 mol) of 2-ethylbutyric acid, 135 g (1.05 mol) of dimethyl sulfate, and 155 g (1.12 mol) of potassium carbonate in 500 ml of acetone was stirred at room temperature under nitrogen overnight, and then was allowed to reflux under nitrogen for 1 hour. The reaction mixture was cooled to room temperature, filtered, and the residual solid was washed with 500 ml of ether. The combined filtrate was concentrated in vacuo, the residue was redissolved in ether, the ether solution was washed successively with water and brine and then dried. The solvent was concentrated and the residual liquid was distilled to afford 70 g (53.8 %) of methyl 2-ethylbutyrate, b.p. 135°-137° C.

1. temperatureto reflux under nitrogen for 1 hour
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationfiltered
4. washthe residual solid was washed with 500 ml of ether
5. concentrationThe combined filtrate was concentrated in vacuo
6. dissolutionthe residue was redissolved in ether
7. washthe ether solution was washed successively with water and brine
8. customdried
9. concentrationThe solvent was concentrated
10. distillationthe residual liquid was distilled

ORD record

ord-f10de9f0097844afabdf27ad78f46ce1

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380729