[CH3:1][O:2][C:3]1[C:12]2[CH:11]3[CH2:13][CH2:14][CH:8]([CH2:9][CH2:10]3)[C:7]=2[C:6]([OH:15])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[CH:23]=[CH2:24].C(OC1C=CC(OC)=C2C=1C1CCC2CC1)C=C.C(OCC=C)C=C.C1(C)C=C(C)C=C(C)C=1>>[CH2:24]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[CH:11]3[CH2:13][CH2:14][CH:8]([CH2:9][CH2:10]3)[C:7]=2[C:6]=1[OH:15])[CH:23]=[CH2:22]Treatment of 8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-5-ol (11.30 g, 0.055 mol) with potassium carbonate (22.94 g, 0.166 mol) and allyl bromide (7.36 g, 0.061 mol) generally according to the procedure described for Intermediate 1 afforded 5-(allyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene. Treatment of the allyl ether in refluxing mesitylene generally according to the procedure described for Intermediate 1 gave 6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalen-5-ol. Treatment of the phenyl with potassium carbonate (20.04 g, 0.145 mol), benzyl bromide (9.09 g, 0.053 mol), and tetrabutylammonium iodide (1.79 g, 0.005 mol) generally according to the procedure described for Intermediate 1 provided 15.05 g (82%) of 6-allyl-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-ethanonaphthalene as a colorless oil. Anal. calcd. for C23H26O2.0.1H2O: C, 82.16; H, 7.85. Found: C, 81.98; H, 7.71.
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