Reaktion #56705

ord-949975933a6846d19c999aa54016fa41

Reaktionsgleichung

CCC[C@@H](C)CCC=C(C)C
(R)-2,6-dimethyl-non-2-ene
O
H2O
CC(C)=O
acetone
O
H2O
→
CCC[C@@H](C)CCC(=O)O
(R)-4-methyl-heptanoic acid

Edukte

—
CrO3
CCC[C@@H](C)CCC=C(C)C
(R)-2,6-dimethyl-non-2-ene
O
H2O
CC(C)=O
acetone
—
CrO3
O
H2O

Reagenzien

Keine

Lösungsmittel

O=S(=O)(O)O
H2SO4
O=S(=O)(O)O
H2SO4
O.[Cl-].[Na+]
brine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe solution extracted with ether
  2. 2
    TrocknenThe combined organic phases were dried (MgSO4)
  3. 3
    Einengenconcentrated

Vorschrift

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%].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419981B2uspto-grants-2008_09