[CH3:1][C:2]1[C:3]([NH:13][C:14](=[O:16])[CH3:15])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[CH2:12])[C:10]=2[CH:11]=1.[OH:17]C1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C(I)C=CC=1.[Na+].[Cl-]>CO.O>[CH3:1][C:2]1[C:3]([NH:13][C:14](=[O:16])[CH3:15])=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][C:12](=[O:17])[CH2:9][C:10]=2[CH:11]=1
In a 50 L mechanically stirred vessel, N-(3-methyl-5-methylene-5,6,7,8-tetrahydronaphthalen-2-yl)acetamide (76) (710 g, 3.30 mol) was suspended in MeOH (22.5 L) and water (1.875 L). A solution of hydroxy(tosyloxy)iodobenzene (1.30 kg, 3.30 mol) in MeOH (3.50 L) was added maintaining the internal temperature below about 20° C. After completion of addition, the solution was stirred for about 15 min and then poured into saturated aqueous NaCl (35 L). The aqueous mixture was extracted with DCM (2×12 L). The combined organic layers were washed with 5 N aqueous HCl (3.50 L), dried with Na2SO4, filtered, and concentrated to afford N-(3-methyl-6-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)acetamide (77) (520 g, 68% yield). 1H NMR (300 MHz, DMSO): δ 9.24 (s, 1H), 7.20 (s, 1H), 6.98 (s, 1H), 3.68 (s, 2H), 2.88 (m, 2H), 2.52 (m, 2H), 2.16 (s, 3H), 2.04 (s, 3H), 1.82 (m, 2H).
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