6-Methoxy-alpha-tetralone → 6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Participants

Reaction Steps

A solution of 6-methoxy-1-tetralone (6.0 g, 0.034 moles) in 48% aqueous hydrobromic acid (80 cm3) was refluxed for 2.5 h. The clear orange solution was then cooled to ice temp. and the resulting preicpitate was filtered off under suction, washed with cold water, and dried to afford the title compound as a pale orange solid (5.16 g, 93%), δH [250 MHz: (CD3)2SO] 1.99 (2H, m), 2.47 (2H, t), 2.82 (2H, t), 6.64 (1H, d), 6.71 (1H, dd), 7.73 (1H, d) and 10.31 (1H, broad s, OH).

Provenance & Evidence