Potassium Hydroxide → 3-{3-[3-(2-Carboxy-2-methylpropyl)benzoyl]-phenyl}-2,2-dimethyl-propanoic acid

HRID 48000

Reaktionsgleichung

Reaktionsgleichung von HRID 48000
[OH-].[K+].C([O:5][C:6](=[O:34])[C:7]([CH3:33])([CH3:32])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15](=[O:31])[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]([C:26]([O:28]CC)=[O:27])([CH3:25])[CH3:24])[CH:17]=2)[CH:10]=1)C>O.C(O)C>[C:26]([C:23]([CH3:25])([CH3:24])[CH2:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[C:15]([C:11]1[CH:10]=[C:9]([CH2:8][C:7]([CH3:33])([CH3:32])[C:6]([OH:34])=[O:5])[CH:14]=[CH:13][CH:12]=1)=[O:31])([OH:28])=[O:27]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 112591923-{3-[3-(2-Ethoxycarbonyl-2-methylpropyl)-benzoyl]phenyl}-2,2-dimethylpropionic acid ethyl ester

Produkt 1

HCID 103624823-{3-[3-(2-Carboxy-2-methylpropyl)benzoyl]-phenyl}-2,2-dimethyl-propanoic acidAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of potassium hydroxide (1.57 g, 28 mmol) in water (1.5 mL) and absolute ethanol (5 mL) was added 3-{3-[3-(2-ethoxycarbonyl-2-methyl-propyl)-benzoyl]-phenyl}-2,2-dimethyl-propionic acid ethyl ester (4.38 g, 10 mmol) in portions. The mixture was heated to reflux for 3 h and the ethanol was distilled off under reduced pressure on a water-bath. The residual aqueous solution was extracted with chloroform (2×50 mL), then cooled with an ice-bath, and acidified with hydrochloric acid to pH 1. The mixture was extracted with diethyl ether (3×50 mL). The ethereal extracts were dried over sodium sulfate and concentrated in vacuo to give 3-{3-[3-(2-carboxy-2-methylpropyl)benzoyl]-phenyl}-2,2-dimethyl-propanoic acid (3.88 g, 100%) as a solid. Mp.: 46-48° C. 1H NMR (300 MHz, CDCl3): δ (ppm): 7.8-7.2 (m, 8H), 2.83 (s, 4H), 1.25 (s,12H). 13C NMR (75 MHz, CDCl3): δ (ppm): 198.02, 184.0, 139.2, 137.3, 134.5, 129.5, 128.4, 128.3, 127.6, 43.8, 24.7. HRMS (LSIMS, gly): Calcd. for C23H27O5 (MH+): 383.1858, found: 383.1858.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 h
  3. distillationthe ethanol was distilled off under reduced pressure on a water-bath
  4. extractionThe residual aqueous solution was extracted with chloroform (2×50 mL)
  5. temperaturecooled with an ice-bath
  6. extractionThe mixture was extracted with diethyl ether (3×50 mL)
  7. dry with materialThe ethereal extracts were dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6b0633f9ec32403eae181b5da9fcd068
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699910B2

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