Isobutyric Acid → 2,2-Dimethyl-3-phenylpropanoic acid

HRID 53651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 53651
[H-].[Na+].C(NC(C)C)(C)C.[C:10]([OH:15])(=[O:14])[CH:11]([CH3:13])[CH3:12].C([Li])CCC.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCCCCC.O.O1CCCC1>[CH3:12][C:11]([CH3:13])([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:10]([OH:15])=[O:14]

Komponenten

9

Edukt 5

HCID 6590Isobutyric AcidHCID 7498Benzyl BromideHCID 7912DiisopropylamineHCID 24758Sodium hydrideHCID 178418339Butyllithium

Produkt 1

HCID 218802,2-Dimethyl-3-phenylpropanoic acidAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 1.23 g (41.0 mmol) of 80% sodium hydride and 50 mL of anhydrous tetrahydrofuran under a nitrogen atmosphere, was added 3.88 g (38.3 mmol) of diisopropylamine and then 3.3 g (37.5 mmol) of isobutyric acid. After heating at reflux for 5 minutes and cooling to 0° C., 15 mL (37.5 mmol) of 2.5M n-butyllithium in hexane was added. The mixture was warmed to 35° C. for 30 min, cooled to 0° C. and 6.40 g (37.5 mmol) of benzyl bromide added. The mixture was stirred for 30 minutes at 0° C., then warmed to 35° C. for one hour and recooled to 0° C. Water was added and the aqueous layer extracted with diethyl ether, acidified with 6N aqueous HCl and extracted with diethyl ether. The organic layer was dried and concentrated to provide 4.0 g of crude product. Chromatography on silica gel using 10% methanol/methylene chloride afforded 1.0 g of pure 2,2-dimethyl-3-phenylpropionic acid, m/e 185 (M+Li).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureat reflux for 5 minutes
  3. temperatureThe mixture was warmed to 35° C. for 30 min
  4. temperaturecooled to 0° C.
  5. temperaturewarmed to 35° C. for one hour
  6. customrecooled to 0° C
  7. extractionthe aqueous layer extracted with diethyl ether
  8. extractionextracted with diethyl ether
  9. customThe organic layer was dried
  10. concentrationconcentrated
  11. customto provide 4.0 g of crude product

Quellen und Nachweise

ORD-Eintrag
ord-8049780ada404a0986abc6374165e118
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620977

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