Acetone → (R)-6-Cyclohexyl-4-methyl-hexanal

HRID 132629

Reaction equation

HRID 132629 reaction equation
[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:17])[CH2:10][CH2:11][CH:12]2[O:14]C2(C)C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)=O.I([O-])(=O)(=O)=O.[K+]>O>[CH:1]1([CH2:7][CH2:8][C@@H:9]([CH3:17])[CH2:10][CH2:11][CH:12]=[O:14])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 516896Potassium periodateHCID 865979603-((R)-5-Cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane

Product 1

HCID 86597961(R)-6-Cyclohexyl-4-methyl-hexanalYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with 10.65 g (44.7 mmol) of 3-((R)-5-cyclohexyl-3-methyl-pentyl)-2,2-dimethyl-oxirane, 70 mL of acetone, 12.3 g (53.6 mmol) of potassium periodate, 70 mL of water, and 0.765 g (4 mmol) of tosic acid-monohydrate. The mixture was stirred for 46 hours. The acetone was removed under reduced pressure, and the mixture was diluted with water. The aqueous layer was extracted with hexanes and dried with sodium sulfate. The drying agent was filtered off and solvent was removed under reduced pressure to get 7.12 g (81% yield) of a clear oil: 1H NMR (400 MHz, CDCl3) ppm 0.87 (m, 5H) 1.13 (m, 3H) 1.25 (m, 5H) 1.66 (m, 8H) 2.40 (m, 2H) 9.75 (s, 1H). MS (APCI) m+1/z is inconclusive.

Workup

  1. customThe acetone was removed under reduced pressure
  2. additionthe mixture was diluted with water
  3. extractionThe aqueous layer was extracted with hexanes
  4. dry with materialdried with sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6b8f5bed32b24deb870c583f9c4eceee
Source dataset
uspto-grants-2008_06
Patent number
US07388023B2

Linked notes

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