Thiophenol → 7-Hydroxy-2-tetralone

Participants

Reaction Conditions

Reaction Steps

Combine 7-methoxy-2-tetralone (5.00 g, 28.3 mmol), thiophenol (3.39 g, 30.8 mmol), K2CO3 (213 mg, 1.54 mmol), and NMP (15 ml) in a round bottom flask equipped with nitrogen inlet. Heat at 180° C. for six hours and then stir at ambient temperature overnight. Treat reaction mixture with 1N aq. NaOH (20 ml) and water (20 ml) before extracting with Et2O. Adjust the alkaline mixture to pH 4 with 1N aq. HCl and extract with Et2O (3×). Dry (MgSO4) the ethereal layer and concentrate to a yellow solid. Purify the crude material on silica gel, eluting with 5% EtOAc/DCM, to obtain 7-hydroxy-2-tetralone (1.88 g) as a light red solid. 1HNMR (CDCl3): 7.09 (d, 1H), 6.69 (d, 1H), 6.62 (s, 1H), 4.86 (s, 1H), 3.53 (s, 2H), 2.99 (t, 2H), 2.54 (t, 2H).

Provenance & Evidence