Acetone → 2-Propenylphenyloxymethyl methyl ketone

A mixture of 7.112 g (50.0 mmol) of 2-propenylphenol (E/Z mixture), 7.041 g of potassium carbonate (50.0 mmol) and 20 ml of acetone was stirred at the boiling point under reflux for 20 minutes. A mixture of 6.94 g (75.0 mmol) of chloroacetone, 0.171 g (1.0 mmol) of potassium iodide and 6.5 ml of acetone which had been activated beforehand by stirring overnight at room temperature was then added to the reaction mixture and the reaction mixture was stirred overnight at the boiling point under reflux. The reaction mixture was cooled to room temperature, added to 50 ml of water and extracted three times with 40 ml each time of diethyl ether. The organic phase was washed with 5% strength sodium hydroxide solution, separated off, dried over Na2SO4 and evaporated. Distillation of the crude product under reduced pressure gave 6.788 g (yield: 67% of theory) of 2-propenylphenyloxymethyl methyl ketone of the formula 2a:

1. temperatureunder reflux for 20 minutes
2. stirringby stirring overnight at room temperature
3. additionwas then added to the reaction mixture
4. stirringthe reaction mixture was stirred overnight at the boiling point
5. temperatureunder reflux
6. extractionextracted three times with 40 ml each time of diethyl ether
7. washThe organic phase was washed with 5% strength sodium hydroxide solution
8. customseparated off
9. dry with materialdried over Na2SO4
10. customevaporated
11. distillationDistillation of the crude product under reduced pressure

ORD-Eintrag

ord-c1169901726341f8961822700365ee8b

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08536344B2