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

HRID 1787413

Reaktionsgleichung

Reaktionsgleichung von HRID 1787413
C([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16]CC2C=CC=CC=2)[C:10]=1[C:24](=[O:26])[CH3:25])C1C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[C:34]([CH:39]=O)[CH:33]=[CH:32]2>>[OH:16][C:11]1[CH:12]=[C:13]([CH3:15])[CH:14]=[C:9]([OH:8])[C:10]=1[C:24](=[O:26])[CH2:25][CH2:39][C:34]1[CH:33]=[CH:32][C:31]2[CH2:30][CH:29]([O:28][CH3:27])[CH2:38][CH2:37][C:36]=2[CH:35]=1

Komponenten

3

Edukt 2

HCID 769916-Methoxy-2-naphthaldehydeHCID 220166451-(2,6-Bisbenzyloxy-4-methylphenyl)ethanone

Produkt 1

HCID 686327651-(2,6-Dihydroxy-4-methyl-phenyl)-3-(6-methoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-3134bb06bc124c018e58493231cca07b
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511021B2

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