Water → 2-Ethylacetoacetamide

To a 500 mL, 5-necked flask, equipped with a circulating jacket, a thermometer, a nitrogen blanket line atop a condenser, an addition funnel, a syringe pump, and a mechanical stirrer, were charged 101.1 g of acetoacetamide (1.00 mol), 100 mL of deionized water and 100 g of methanol. The mixture was stirred at ambient temperature until all solids were dissolved. A 45% aqueous potassium hydroxide solution (99.6 g, 0.80 mol) was then added to the above solution through the addition funnel over a period of 5 minutes. The resulting mixture was stirred for 30 minutes and then cooled to 15° C. Ethyl bromide (130.8 g, 1.20 mol) was added to the mixture through the syringe pump over a period of 30 minutes. The resulting mixture was stirred at 15° C. for 16 hours. All volatiles were then removed at 60° C./20 mmHg. The solid residue was dissolved in 300 mL of water and extracted with chloroform. A total of six chloroform extractions were performed (60 mL+5×200 mL). The first extraction contained a high level of 2,2-diethylacetoacetamide and was discarded. The remaining extraction solutions were combined. After chloroform was removed in vacuo, 67.7 g of 2-ethylacetoacetamide was obtained. Crude yield: 66% (based on KOH charge).

1. customTo a 500 mL, 5-necked flask, equipped with a circulating jacket
2. dissolutionwere dissolved
3. stirringThe resulting mixture was stirred for 30 minutes
4. temperaturecooled to 15° C
5. stirringThe resulting mixture was stirred at 15° C. for 16 hours
6. customAll volatiles were then removed at 60° C./20 mmHg
7. dissolutionThe solid residue was dissolved in 300 mL of water
8. extractionextracted with chloroform
9. extractionA total of six chloroform extractions
10. extractionThe first extraction
11. extractionThe remaining extraction solutions
12. customAfter chloroform was removed in vacuo

ORD record

ord-8058a3fdca864b89b01de3087aa4af3a

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05922916