Carbon Dioxide → 2,6-diisopropylbenzoic acid

HRID 1756769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756769
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1I)([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.[C:25](=[O:27])=[O:26].[OH-].[Na+]>C(OCC)C.O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[C:25]([OH:27])=[O:26])([CH3:3])[CH3:2]

Komponenten

8

Edukt 5

HCID 280Carbon DioxideHCID 8058HexaneHCID 14798Sodium HydroxideHCID 99259602-Iodo-1,3-diisopropylbenzeneHCID 178418339Butyllithium

Produkt 1

HCID 119589902,6-diisopropylbenzoic acidAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5.09 g (17.7 mmol) of 2, 6-diisopropylphenyl iodide in 70 ml of dry ethyl ether was dropwise added 1.6M solution of n-butyllithium in hexane (11.1 ml, 17.8 mmol) at -20° C. The reaction mixture was allowed to warm at 0° C., stirred for 1 hour and poured onto about 100 g of pulverized dry ice. The mixture was allowed to warm gradually to room temperature, mixed with 50 ml of water and the aqueous layer was made alkaline with aqueous sodium hydroxide. The organic layer was separated, and the aqueous layer was washed with ethyl ether, acidified With conc. hydrochloric acid and extracted with ethyl ether. The extract was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent evaporated to give 2.53 g of 2, 6-diisopropylbenzoic acid as white solid.

Aufarbeitung

  1. customat -20° C
  2. temperatureto warm gradually to room temperature
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with ethyl ether
  5. extractionextracted with ethyl ether
  6. washThe extract was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-04f7a9d7a4fd48079b1ac35638ab2f7f
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05442060

Notizen zur Reaktion

Wird geladen…