Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:10]([CH3:12])[CH3:11])[CH:3]=1.C([Li])(C)(C)C.[CH3:18][C:19]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([CH3:29])[C:20]=1C=O.[O:30]1CCC[CH2:31]1>CCOCC>[CH3:29][C:23]1[CH:24]=[C:25]([O:27][CH3:28])[CH:26]=[C:19]([CH3:18])[C:20]=1[O:30][CH2:31][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH:10]([CH3:12])[CH3:11])[CH:3]=1
To 4-bromo-2-isopropylanisole (3) (12 g, 52.4 mmol) in 300 mL of tetrahydrofuran at -78° C. was added 68 mL of tert-Butyllithium (1.7M in pentane). The reaction mixture was stirred for 10 min at -78° C. and then 2,6-dimethyl-4-methoxybenzaldehyde (6) (8.6 g, 52.4 mmol) was added. The reaction mixture was stirred for 1 hour at -78° C. and for 1.5 hours at room temperature, diluted with 150 mL of ether, washed with 150 mL of water, acidified with 1N HCl, and washed with 5×50 mL of brine. The organic portion was dried (MgSO4), filtered, and evaporated to give the crude product, which was purified by flash column chromatography (silica gel, 95:5 hexane/ethylacetate) to yield 3,5-dimethyl-4-(3'-isopropyl-4'-methoxybenzylhydroxy) anisole (7) (12 g, 38.2 mmol, 73%) as an oil; 1HNMR (CDC13) δ 1.2 (dd, 6H), 2.27 (s, 6H), 3.30 (heptet, 1H), 3.80 (s, 6H), 6.26 (s, 1H), 6.59 (s, 2H) 6.76 (d, 1H), 6.89 (d, 1H), 7.24 (s, 1H).
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