Phenol → 5-Ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

HRID 1975789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975789
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13].[Al+3].[Cl-].[Cl-].[Cl-].[C:18]1(O)C=CC=CC=1.[CH2:25](I)C.C(=O)([O-])[O-].[K+].[K+].C1(=O)C2C(=CC=CC=2)CCC1.[CH3:45][O:46][C:47]1[CH:56]=[CH:55][CH:54]=[C:53]2[C:48]=1[CH2:49][CH2:50][CH2:51][CH:52]2[C:57]([OH:59])=[O:58]>C1C=CC=CC=1.CC(C)=O>[CH2:1]([O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:13])[CH3:18].[CH2:45]([O:46][C:47]1[CH:56]=[CH:55][CH:54]=[C:53]2[C:48]=1[CH2:49][CH2:50][CH2:51][CH:52]2[C:57]([OH:59])=[O:58])[CH3:25]

Komponenten

11

Edukt 7

HCID 996PhenolHCID 6340IodoethaneHCID 107241-TetraloneHCID 11430Potassium CarbonateHCID 366205-MethoxytetraloneHCID 6451240Aluminum(III) ChlorideHCID 107034695-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic Acid

Produkt 2

HCID 190984695-Ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acidHCID 218967975-Ethoxy-1-tetralone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 241BenzeneLösungsmittel

Versuchsvorschrift

5-Ethoxy-1-tetralone was prepared from the commercially available 5-methoxy-1-tetralone by treatment with AlCl3 in benzene followed by alkylation of the resulting phenol with ethyl iodide in acetone in the presence of potassium carbonate. The resulting tetralone was then treated by the procedures described in International Patent Application Number WO 89/06645 for the preparation of 5-methoxy 1,2,3,4-tetrahydronaphthalene-1-carboxylic acid to yield 5-ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid. The title compound was prepared from 5-ethoxy-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid by the procedures described in Example 10 through 15 to yield the product as a white solid. m.p. 219°-221° C. 1H NMR (DMSO-b6, 300 MHz) δ1.32 (t, 3H), 1.65-1.9 (m, 4H), 2.4-2.7 (m, 2H), 2.59 (s, 3H), 3.0-3.3 (m, 3H), 4.0 (m, 2H), 6.78 (d, 1H), 6.84 (d, 1H), 7.12 (t, 1H), 8.6 (bs, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-d4a59f64970f428cb55a6067bb119372
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288749

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