Tetrahydrofuran → HCID 24261623, compound

Participants

Reaction Conditions

Reaction Steps

This compound was previously prepared by a two-step process.v However, we prepared it by a one-step method adapted from another literature procedure.vi Neat 3,5-dimethoxybenzonitrile (16.0 g, 98.1 mmol) was added to a 2.0M solution of phenylmagnesium chloride in THF (98.0 mL, 196.1 mmol). The reaction mixture was refluxed for 24 hours at 70° C. The solution was then transferred into a mixture of concentrated aqueous HCl (100 mL) and ice (300 g). The mixture was allowed to warm up to room temperature and stirred for 24 hours. The product was extracted with ether (3×300 mL) and the combined organic layers were washed with brine (200 mL) and water (150 mL) before being dried with anhydrous magnesium sulfate. The filtrate was dried in vacuo to afford 3,5-dimethoxybenzophenone as a yellow solid in 75% yield. 1H NMR (CDCl3): δ 7.84 (d, 3JH-H=7.2 Hz, 1H), 7.61 (t, 3JH-H=7.6 Hz, 2H), 7.50 (t, 3JH-H=7.6 Hz, 2H), 6.95 (d, 3JH-H=2.4 Hz, 1H), 6.70 (t, 3JH-H=2.4 Hz, 2H), 3.85 (s, 6H).

Provenance & Evidence