Hydrochloric Acid → HCID 14491495, compound

Participants

Reaction Steps

To an ice cold, stirred solution of the above crude β-(1-bromo-2-naphthyl)propionyl chloride in 802 mL of dry CH2 Cl2 was added 26.11 g of anhydrous AlCl3 carefully. The reaction mixture was refluxed for 2 h, cooled to room temperature and treated carefully while stirring with 900 mL of ice-water followed by 75 mL of conc. HCl. The brown precipitate was filtered and washed five times with small portions of CH2Cl2. The aqueous layer was separated and extracted twice with 100-mL portions of CH2Cl2. The combined CH2Cl2 extracts were washed three times with small portions of H2O, dried (MgSO4) and evaporated from a water bath (50°-60° C.) with a rotary evaporator (7 mm) to give 30.1 g (80.1%) of the crude ketone as a yellow solid, mp 146°-149° C., which could be recrystallized from acetic acid to give 28.5 g (76%) of the pure ketone as colorless crystals, mp 149°-151° C.

Provenance & Evidence