Acetone → 4-Methylheptanoic acid, (-)-

HRID 28427

Reaktionsgleichung

Reaktionsgleichung von HRID 28427
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@H](C)CCC)[CH3:3].[OH2:12].C[C:14]([CH3:16])=[O:15]>OS(O)(=O)=O.[Cl-].[Na+].O>[CH3:1][C@H:2]([CH2:4][CH2:5][CH3:6])[CH2:3][CH2:16][C:14]([OH:12])=[O:15]

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 962Water2×HCID 15345839(6R)-2,6-Dimethylnon-2-ene

Produkt 1

HCID 138003704-Methylheptanoic acid, (-)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To (R)-2,6-dimethyl-non-2-ene (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave (R)-4-methyl-heptanoic acid as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%].

Aufarbeitung

  1. extractionthe solution extracted with ether
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-949975933a6846d19c999aa54016fa41
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419981B2

Verknüpfte Notizen

Wird geladen…