Hydrochloric Acid → 4-(4-Bromophenoxy)cyclohexanone

Participants

Reaction Conditions

Reaction Steps

1 N HCl(aq) (45 mL) was added to a solution of 8-(4-bromophenoxy)-1,4-dioxaspiro[4.5]decane (2.8 g, 8.94 mmol) in THF (100 mL). The reaction was heated to 50° C. After 1 hour the reaction was cooled to room temperature and neutralized by addition of solid sodium bicarbonate. The reaction was extracted with ether (1×), the resulting organic layer was washed with water, dried (Na2SO4), filtered and concentrated. Purification on a Biotage SNAP cartridge KP Sil 100 g (hexanes/ethyl acetate=9:1) afforded the title compound as a white solid (2.09 g, 87%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.02-2.13 (m, 2H) 2.21-2.41 (m, 4H) 2.61-2.74 (m, 2H) 4.62-4.71 (m, 1H) 6.81-6.89 (m, 2H) 7.37-7.44 (m, 2H)

Provenance & Evidence