Réaction #56705

ord-949975933a6846d19c999aa54016fa41

Équation de réaction

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

Réactifs

—
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

Réactifs

Aucun

Solvants

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

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionthe solution extracted with ether
  2. 2
    SéchageThe combined organic phases were dried (MgSO4)
  3. 3
    Concentrationconcentrated

Mode opératoire

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%].

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07419981B2uspto-grants-2008_09