Ethyl isovalerate → HCID 13374430, compound

Temperature

112 °C

To a solution of 2.99 g (0.13 g. atm) of sodium in 50 ml of absolute ethanol, heated to 60° C., was added 11.81 g (0.09 m) of 3-methyl-benzyl cyanide followed by the slow addition, over a period of 20 minutes of 31.27 g (0.24 m) of ethyl isovalerate. The reaction mixture was heated under reflux overnight (18 hrs.). During this period the color of the solution turned from yellow to dark orange. After approximately 70 ml of solvent and excess of ethyl valerate was removed by distillation, 75 ml of toluene was added and additional 30 ml of the solvent was removed by heating the mixture to 112° C. The reaction mixture was cooled, diluted with 100 ml of toluene and was washed twice with water. The aqueous extracts were combined and acidified with 6N hydrochloric acid. The product was extracted in 300 ml of methylene chloride. The organic extract was washed with water, dried over magnesium sulfate and was concentrated under vacuum to afford 18.56 g of orange colored oil. Crystallization from ethyl acetate hexane solution afforded 14.0 g. of a white solid. m.p. 46.5°-50° C.

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux overnight (18 hrs.)
3. waitDuring this period the color of the solution turned
4. customAfter approximately 70 ml of solvent and excess of ethyl valerate was removed by distillation, 75 ml of toluene
5. additionwas added
6. customadditional 30 ml of the solvent was removed
7. temperatureThe reaction mixture was cooled
8. additiondiluted with 100 ml of toluene
9. washwas washed twice with water
10. extractionThe product was extracted in 300 ml of methylene chloride
11. extractionThe organic extract
12. washwas washed with water
13. dry with materialdried over magnesium sulfate
14. concentrationwas concentrated under vacuum

ORD record

ord-0d962f1953064af9a1ac45a927019d59

Source dataset

uspto-grants-1984_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04469688