Acetone → 4-Methylheptanoic acid, (-)-

HRID 1795526Notes

Reaction equation

HRID 1795526 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-b0ffe542d1fb451d8d73643f9cd83f81
Source dataset
uspto-grants-2006_04
Patent number
US07026505B2

Reaction notes

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