Phenacyl bromide → HCID 58122284, compound

Participants

Reaction Conditions

Reaction Steps

1.36 g (−)-β-pinene (10 mmol) was dissolved in 5 ml THF. 21 ml of a 0.5-molar solution of 9-BBN in THF (10.5 mmol) was added to this solution at 0° C. The reaction mixture was slowly brought to room temperature and stirred for a further 3 hours. The resulting solution was cooled to −78° C., and a solution of 1.12 g potassium tert-butanolate (10 mmol) in 10 ml THF was then added to the cooled reaction solution. After a short time, 2 g α-bromacetophenone (10 mmol) was added in portions with constant stirring. The reaction mixture was slowly brought to room temperature and stirred for 4 hours at room temperature. The resulting product mixture had 50 ml n-pentane added to it, and washed three times in each case with 10 ml of a 3N sodium hydroxide solution and with 10 ml water. The organic phase was dried over magnesium sulfate. Solvent was removed from the filtrate at reduced pressure. The raw product was purified by column chromatography. 140 mg (10%) of the aforesaid product was obtained.

Provenance & Evidence