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4-Formylbenzoic acid → 4-[3-(8,8-Dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-oxopropenyl]benzoic acid

HRID 613347
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 613347
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([C:18](=[O:20])[CH3:19])=[CH:15][CH:16]=3)[C:11]([CH3:22])([CH3:21])[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[C:23]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)([OH:25])=[O:24].[OH-].[Na+]>CO>[O:20]=[C:18]([C:14]1[CH:15]=[CH:16][C:17]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:9][CH2:10][C:11]([CH3:22])([CH3:21])[C:12]=2[CH:13]=1)[CH:19]=[CH:30][C:29]1[CH:32]=[CH:33][C:26]([C:23]([OH:25])=[O:24])=[CH:27][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 120884-Formylbenzoic acidHCID 14798Sodium HydroxideHCID 223237763,4-Dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene2×

Produkt 1

HCID 542966524-[3-(8,8-Dimethyl-5-p-tolyl-7,8-dihydro-2-naphthyl)-3-oxopropenyl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 78.7 mg (0.272 mmol) 3,4-dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene (Compound 100G) in 4.0 ml of MeOH was added 53.1 mg (0.354 mmol) of 4-carboxy benzaldehyde, and 80. mg (2.00 mmol; 2.0 ml of 1M aqueous NaOH). The resulting solution was stirred at room temperature for 12 hours, concentrated under reduced pressure, and the residual oil dissolved in EtOAc. The solution was treated with 10% HCl, and the organic layer was washed with H2O, and saturated aqueous NaCl, then dried over Na2SO4. Removal of the solvents under reduced pressure gave the title compound as a colorless solid which was purified by recrystallization from CH3CN. 1H NMR (acetone-d6): δ 8.00 (7H, m), 7.83 (1H, d, J=15.6 Hz), 7.24 (4H, s), 7.13 (1H, d, J=8.1 Hz), 6.12 (1H, t, J=4.5 Hz), 2.42 (2H, d, J=4.8 Hz), 2.38 (3H, s), 1.41 (6H, s).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residual oil dissolved in EtOAc
  3. additionThe solution was treated with 10% HCl
  4. washthe organic layer was washed with H2O, and saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvents under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-683867a1e5004fc69d2514495e668a45
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06008204

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