Acetone → 4-Methylheptanoic acid, (-)-

HRID 1167910Notes

Reaction equation

HRID 1167910 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 138003704-Methylheptanoic acid, (-)-

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To alkene 98 (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 the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%].

Workup

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

Sources & evidence

ORD record
ord-ccc51ca9814e49d0a78c9a3593dc672b
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

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