Water → (4R)-6-cyclohexyl-4-methylhexanoic acid

HRID 132630Notes

Reaction equation

HRID 132630 reaction equation
[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:14])[CH2:10][CH2:11][CH:12]=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.[Mn]([O-])(=O)(=O)=[O:17].[K+].S(=O)(O)[O-].[Na+]>C(O)(=O)C.CC(C)=O>[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:14])[CH2:10][CH2:11][C:12]([OH:17])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 86597961(R)-6-Cyclohexyl-4-methyl-hexanal

Product 1

HCID 69266999(4R)-6-cyclohexyl-4-methylhexanoic acidYield 54.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

A flask was charged with 7.12 g (36.3 mmol) of (R)-6-cyclohexyl-4-methyl-hexanal, 40 mL of water, 20 mL of acetone, 4 mL acetic acid, and 6.18 g (39.9 mmol) of potassium permanganate. The mixture was stirred vigorously overnight. The mixture was then treated with sat. aqueous sodium bisulfite until the liquid became clear. The liquid was extracted with hexanes. The combined hexane layers were washed with sat. aqueous sodium bisulfite until the hexane layer was clear. The hexane phases were dried with magnesium sulfate. The drying agent was filtered off and the solvent was removed under reduced pressure, which yielded 4.17 g (54% yield) of a clear oil: 1H NMR (400 MHz, CDCl3) ppm 0.89 (m, 5H), 1.13 (m, 3H) 1.25 (m, 5H) 1.66 (m, 8H) 2.40 (m, 2H). MS (APCI) m+1/z=211.

Workup

  1. extractionThe liquid was extracted with hexanes
  2. washThe combined hexane layers were washed with sat. aqueous sodium bisulfite until the hexane layer
  3. dry with materialThe hexane phases were dried with magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was removed under reduced pressure, which

Sources & evidence

ORD record
ord-e2382c81b9bf46018082afaf5de4632f
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Reaction notes

Loading…