Methanol → Ethyl 3-methyl-2-(2-oxoethyl)butanoate

In 100 g of methanol were dissolved 10.0 g of ethyl α-allylisovalerate (general formula [XI] wherein R=--CH2CH3) and, under cooling at -20°~-10° C. and stirring, ozone gas was bubbled into the solution for 8 hours. Then, at room temperature, the reaction mixture was added to 100 g of dimethyl sulfide and the mixture was stirred at that temperature overnight. The reaction mixture was then distilled under reduced pressure to remove the low-boiling fraction and the residue was diluted with 50 g of diethyl ether. Following the addition of 4 g of anhydrous calcium chloride, hydrogen chloride gas was bubbled into the mixture at room temperature for 10 minutes. Then, 5 g of anhydrous potassium carbonate were added and the mixture was thoroughly stirred. The diethyl ether solution was taken, washed with water, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the low-boiling fraction. By the above procedure there were obtained 9.0 g of ethyl 2-isopropyl-3-formyl-propionate (general formula [XII] wherein R=--CH2CH3) yield: 89% based on ethyl α-allylisovalerate; the NMR spectrum of the aldehyde (60 MHz) δHMSCDCl3 : 9.74].

1. temperatureunder cooling at -20°~-10° C.
2. customozone gas was bubbled into the solution for 8 hours
3. additionThen, at room temperature, the reaction mixture was added to 100 g of dimethyl sulfide
4. stirringthe mixture was stirred at that temperature overnight
5. distillationThe reaction mixture was then distilled under reduced pressure
6. customto remove the low-boiling fraction
7. additionthe residue was diluted with 50 g of diethyl ether
8. additionthe addition of 4 g of anhydrous calcium chloride, hydrogen chloride gas
9. customwas bubbled into the mixture at room temperature for 10 minutes
10. additionThen, 5 g of anhydrous potassium carbonate were added
11. stirringthe mixture was thoroughly stirred
12. washwashed with water
13. dry with materialdried over anhydrous magnesium sulfate
14. distillationdistilled under reduced pressure
15. customto remove the low-boiling fraction

ORD record

ord-c2686a5adb414753aa6c3fedeaa8c7c6

Source dataset

uspto-grants-1983_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04409238