[CH2:1]([C:5]1([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15]C)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].[Br-].[Al+3].[Br-].[Br-].Cl.C(OCC)C>C1C=CC=CC=1>[CH2:1]([C:5]1([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[OH:15])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]A mixture of 2,2-dibutyl-3,4-dihydro-5-methoxy-1(2H)-naphthalenone (2.321 g) and aluminium bromide (7.0 g) in dried benzene (40 ml) was refluxed for 40 minutes and allowed to cool in an ice-water bath. The cooled mixture was poured into a mixture of 1N aqueous hydrochloric acid (150 ml) and diethyl ether (100 ml) with stirring. The organic layer was washed with brine, dried, and concentrated in vacuo to yield 2,2-dibutyl-3,4-dihydro-5-hydroxy-1(2H)-naphthalenone (2.643 g) as a crude syrup.
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