[CH3:1][C:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([OH:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]=[CH2:20].C(OC1C=CC(C)=C2C=1CCC2)C=C.C(OCC=C)C=C>C1(C)C=C(C)C=C(C)C=1>[CH2:20]([C:4]1[CH:3]=[C:2]([CH3:1])[C:10]2[CH2:9][CH2:8][CH2:7][C:6]=2[C:5]=1[OH:11])[CH:19]=[CH2:18]Treatment of 7-methylindan-4-ol (10.00 g, 0.067 mol) with potassium carbonate (37.3 g, 0.270 mol) and allyl bromide (9.80 g, 0.081 mol) generally according to the procedure described for Intermediate 1 afforded 4-(allyloxy)-7-methylindane. Refluxing the allyl ether in mesitylene generally according to the procedure described for Intermediate 1 gave 5-allyl-7-methylindan-4-ol. Treatment of the phenyl with potassium carbonate (27.99 g, 0.203 mol) and benzyl bromide (12.70 g, 0.074 mol) generally according to the procedure described for Intermediate 1 provided 8.41 g (45%) of 5-allyl-4-(benzyloxy)-7-methylindane as a colorless oil. Rf=0.42 (silica, ethyl acetate:hexanes 1:19); Anal. calcd. for C20H22O.0.3H2O: C, 84.65; H, 8.03. Found: C, 84.64; H, 7.78.
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