Sodium Iodide → HCID 68500397, compound

Participants

Reaction Steps

To a suspension of 4-hydroxybenzophenone (4.0 g, 19.8 mmol) in CH3CN (30 mL) was added K2CO3 (8.20 g, 59.3 mmol). The mixture was refluxed under nitrogen for 1 h. Cooled to room temperature, 2-(2-chloroethoxy)ethanol (4.3 mL, 39.6 mmol) was added, followed by addition of NaI (3.00 g, 19.8 mmol). The reaction mixture was refluxed under nitrogen overnight. The mixture was cooled to room temperature and EtOAc (50 mL) was added. The precipitated white solid was filtered and washed with EtOAc (50 mL). The filtrate was transferred to a separatory funnel and washed with 1 N NaOH, water, brine and dried over Na2SO4. Concentration yielded a yellow oil which was further purified by chromatography on a silica gel column eluted with a gradient from hexanes to 70% EtOAc:hexanes to give 7 as colorless crystals (4.96 g, 88%). mp 31-32° C. 1H NMR (400 MHz, CDCl3): δ 3.65-3.75 (m, 2H), 3.75-3.80 (m, 2H), 3.90-3.95 (m, 2H), 4.20-4.25 (m, 2H), 6.99 (d, J=8.8 Hz, 2H), 7.45-7.50 (m, 2H), 7.55-7.60 (m, 1H), 7.70-7.80 (m, 2H), 7.83 (d, J=8.8 Hz, 2H). LRMS (ESI): m/z 287 (M+H)+.

Provenance & Evidence