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

HRID 1787412

Reaktionsgleichung

Reaktionsgleichung von HRID 1787412
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.[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[CH:37]=O>>[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][CH2:37][C:28]1[CH:29]=[CH:30][C:31]2[CH2:32][CH2:33][CH2:34][CH2:35][C:36]=2[CH:27]=1

Komponenten

3

Edukt 2

HCID 62012-NaphthalenecarboxaldehydeHCID 220166451-(2,6-Bisbenzyloxy-4-methylphenyl)ethanone

Produkt 1

HCID 220166891-(2,6-Dihydroxy-4-methyl-phenyl)-3-(5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one

Versuchsvorschrift

The intermediate, 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-ethanone, was treated with 2-naphthaldehyde 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-(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 (400 MHz, CD3OD) δ 7.02 (s, 1H), 6.93 (m, 2H), 6.87 (s, 1H) 6.61 (s, 1H), 5.24 (d, J=7.73 Hz, 1H), 3.94 (d, J=12.05 Hz, 1H), 3.75-3.34 (m, 5H), 3.25-2.72 (m, 8H), 2.43 (s, 3H), 1.81-1.77 (m, 4H). MS: m/z (MH+) 469.

Quellen und Nachweise

ORD-Eintrag
ord-332f061087324574bde7861097887232
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511021B2

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