Hydrogen Peroxide → 2-Allyloctanoic acid

Participants

Reaction Steps

An aqueous solution of hydrogen peroxide (31% by weight; 0.6 ml, 5.6 mmol) and 0.047 g (1.1 mmol) of lithium hydroxide monohydrate were added dropwise to a solution of 0.20 g (0.56 mmol) of N-ethyloxycarbonyl-N-(2-allyloctanoyl)-(R)-1-phenylethylamine (diastereomer ratio (1R,2S):(1R,2R)=81:19) in a mixture of 4 ml of THF and 1 ml of water on an ice bath. The mixture was stirred on an ice bath for 1 hour and then at room temperature for 18 hours. A 2 N aqueous solution of sodium sulfite (10 ml) was added dropwise to the reaction mixture on an ice bath, and the resulting mixture was stirred at room temperature for 1 hour. Water (15 ml) was added to the reaction mixture, and the whole mixture was washed with 5 ml of ethyl acetate. To the aqueous layer was added 6 ml of a 1 N aqueous solution of hydrochloric acid (pH=2), and the resulting mixture was extracted with two 40-ml portions of ethyl acetate. The organic layer was concentrated under reduced pressure to give 0.043 g (42%, 62% ee) of the title compound as a colorless oil.

Provenance & Evidence