Sodium Hydroxide → Diphenyl Ether

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromopyridinol 1 (7.6 g, 44 mmol) in 1N aqueous sodium hydroxide (44 mL, 44 mmol) was stirred at room temperature for 30 minutes. Phenylglycidol 2 (5.0 g, 33 mmol) was added in one portion and the reaction mixture was heated at 75° C. for 5 h. The reaction mixture was brought to room temperature and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulphate, filtered and solvent was removed under reduced pressure. The reaction product was purified on silica gel (eluent 1:1 hexanes/ethyl acetate) to give the diol 3 (7.5 g, 69%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.90 (m, 1H), 7.36 (m, 5H), 7.00 (m, 1H), 6.92 (m, 1H), 5.32 (d, 1H), 4.00 (m, 2H), 3.84 (m, 1H), 2.94 (m, 1H), 2.60 (m, 1H).

Provenance & Evidence