[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].Cl[CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:19]([CH3:24])([CH3:23])[CH2:18][CH2:17][C:16]([CH3:26])([CH3:25])[C:15]=2[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.[I-].[Na+]>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:19]([CH3:24])([CH3:23])[CH2:18][CH2:17][C:16]([CH3:26])([CH3:25])[C:15]=2[CH:14]=1)[CH:5]=[O:6]
3,4-Dihydroxybenzaldehyde (0.580 g., 4.20 mmol, 1 equiv.) is dissolved in 4.2 mL of acetone. 2-Chloromethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene) (18a) (1.00 g., 4.20 mmol, 1 equiv.), sodium iodide (0.020 g., 0.133 mmol, 0.03 equiv.), and potassium carbonate (0.580 g., 4.20 mmol, 1 equiv.) are added, and the mixture is heated to reflux for 19 hours. The mixture is poured into water, and extracted twice with ether, and once with EtOAc. The combined extracts are washed with brine, dried (MgSO4), and concentrated. The crude material is chromatographed on silica gel using EtOAc/hexane as the eluent to afford 3-hydroxy-4-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy benzaldehyde (41) (0.666 g., 1.97 mmol, 47%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 9.87 (s, 1H, CHO), 7.48-7.35 (m, 4H, ArH), 7.22 (dd, J= 2, 8 Hz, 1H, ArH), 7.09 (d, J=8 Hz, 1H, ArH), 5.14 (s, 2H, ArCH2O), 1.72 (s, 4H, CH2CH2), 1.32 (s, 6H, 2×CH3), 1.31 (s, 6H, 2×CH3); 13C NMR (75 MHz, CDCl3) δ 191.00 (C=0), 151.20, 146.33, 145.79, 145.53, 132.11, 130.76, 127.17, 126.53, 125.51, 124.31, 114.28, 111.42, 71.60, 34.92, 34.26, 31.82; IR (KBr) 3342, 2962, 2932, 1682, 1608, 1582, 1512, 1278, 1112 cm-1 ; MS (DCI) m/e 339 (MH+), 201 (C15H21+).
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