Water → (4-Hydroxyphenyl)(4-iodophenyl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of (4-Iodophenyl)[4-(methyloxy)phenyl]methanone (142) (1.50 g, 4.44 mmol) and AlCl3 (2.40 g, 17.74 mmol) were refluxed in benzene (50 mL) for 1.5 h and then cooled to 0° C. in an ice bath. Water (50 mL) was added slowly, and the mixture was extracted with ether (2×100 mL). The combined ethereal extracts were washed with water, brine, and dried over Na2SO4. Concentration and trituration with hot hexanes afforded 1.36 g (95%) of the title compound as light brown solid. 1H NMR (400 MHz, CDCl3): δ 5.37 (br s, 1H), 6.90 (d, J=8.6 Hz, 2H), 7.47 (d, J=8.4 Hz, 2H), 7.75 (d, J=8.6 Hz, 2H), 7.83 (d, J=8.5 Hz, 2H). LCMS (ESI): m/z, 325 (M+H)+, 323 (M−H)−.

Provenance & Evidence