Ethanol → HCID 54264942, compound

Temperature

0 °C

A dry 25 ml two-necked round bottom flask was equipped with a stirring bar, addition funnel, reflux condenser and nitrogen bubbler. The flask was charged with absolute ethanol (9.2 gm, 200 mmoles) and the addition funnel charged with thionyl chloride (4.3 gm, 36 mmoles). The flask and its contents were cooled to about 0° C. The thionyl chloride was added dropwise while maintaining the flask temperature at 5° C. or below. After the addition was completed, the resulting mixture was stirred for 1 hour at 0° C. Beta-chloroethylideneaminooxyacetic acid (2.7 gm, 18 mmoles) was added in one portion. The resulting mixture was allowed to warm to room temperature during 1 hour. The flask was warmed to 40°-45° C. and maintained for 4 hours. The resulting mixture was cooled, then solvents were removed in vacuo. The residue was taken up in ethyl acetate which was extracted with an aqueous solution of sodium bicarbonate. The ethyl acetate layer was dried over magnesium sulfate, filtered, then taken to "dryness" in vacuo. A brown oil (2.1 gm) was obtained. Distillation at 0.5 mm Hg gave the desired product as a clear oil (2.0 gm), b.p. 60°-70° C.

1. customA dry 25 ml two-necked round bottom flask was equipped with a stirring bar, addition funnel
2. temperaturereflux condenser
3. temperaturewhile maintaining the flask temperature at 5° C. or below
4. additionAfter the addition
5. temperatureto warm to room temperature during 1 hour
6. temperatureThe flask was warmed to 40°-45° C.
7. temperaturemaintained for 4 hours
8. temperatureThe resulting mixture was cooled
9. customsolvents were removed in vacuo
10. extractionwas extracted with an aqueous solution of sodium bicarbonate
11. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
12. filtrationfiltered

ORD record

ord-a08521b5765c44afa485c4ee9e61861c

Source dataset

uspto-grants-1986_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04584014