Hydrogen Bromide → 6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-methoxytetralone (8.8 g, 50 mmol) and 48% hydrobromic acid (25 mL) in acetic acid (25 mL) was refluxed at 125° C. for 3 hours. The mixture was then poured into ice/water and extracted with ethyl acetate (125 mL). The extract was washed with water and brine, dried over MgSO4, and concentrated in vacuo. To the residue was added CH2Cl2 (25 mL), and the suspension was cooled at 0° C. for 2 hours. The solid was filtered and washed with cold CH2Cl2 to afford 5.8 g of 6-hydroxytetralone.

Provenance & Evidence