Allyl bromide → 5-Allyl-7-methylindan-4-ol

Participants

Reaction Steps

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.

Provenance & Evidence