A simple synthesis of 2-acetyl-5-hydroxy-1,2,3,4-tetrahydronaphthalene

2006 ARKIVOC  
5-Methoxy-1-tetralone 1 has been converted into 2-Acetyl-5-methoxy-1,2,3,4tetrahydronaphthalene 5 by acylation, hydrogenation and oxidation respectively. Demethylation of 5 with boron tribromide afforded the title compound 6. ARKAT g, 77%), m.p. 50-53 o C; I.R. ‫ט‬ max (cm -1 ): 1672 (CO) and 1582 (C=C); MS (m/z): 218 (M + Issue in Honor of Prof. Atta-ur-Rahman ARKIVOC 2007 (vii) 8-11 ARKAT 2-Acetyl-5-hydroxy-1,2,3,4-tetrahydronaphthalene (6). To a solution of compound 5 (300 mg, 1.5 mmol) in
more » ... chloromethane (3 mL) cooled at -10 o C was added BBr 3 (1.7 mL, 1M BBr 3 in dichloromethane) and the mixture was stirred under nitrogen for 30 min at -10 o C and then at room temperature for 30 min. The reaction mixture was diluted with water, stirred for 20 min and extracted with chloroform. The organic extract was washed with brine and evaporated. The resulting material was chromatographed over silica gel with hexane:ether (1:1) to give the compound 6 (130 mg, 46%), m.p. 103-105 o C (lit. 2 106-107 o C); I.R. ‫ט‬ max (cm -1 ): 3392 (OH), 1701 (CO); MS (m/z): 190 (M +
doi:10.3998/ark.5550190.0008.702 fatcat:g7b6thbiwvh2jn4ixxpq4atmqa