Acetone → 4-Methylheptanoic acid, (-)-

HRID 130532

Reaction equation

HRID 130532 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-bf9b1fd46063406582f2686e97772940
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Linked notes

Loading…