6-Methoxy-2-naphthaldehyde → 1-(2,6-Dihydroxy-4-methyl-phenyl)-3-(6-methoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one

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Reaction Steps

Intermediate 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-ethanone, was treated with 6-methoxynaphthalene-2-carbaldehyde as described in Example 1, Part B. Subsequent catalytic hydrogenation as described in Example 1, Part C, provided 1-(2,6-dihydroxy-4-methyl-phenyl)-3-(6-methoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one as a by-product. Further treatment of this by-product as described in Example 1, Part D and E, afforded the title compound. 1HNMR (300 MHz, CD3COCD3) δ 7.2-7.0(m, 2H), 6.95-6.85(m 3H), 6.6(s, 1H), 5.6(s, 1H), 5.27(d, J=7 Hz, 1H), 3.95-3.85(m, 1H), 3.75-3.55(m, 6H), 3.37(s, 3H), 3.3-3.2(m, 1H), 3.1-2.6(m, 8H), 2.05(s, 3H). MS: m/z (MH+) 499.

Provenance & Evidence