(S)-2,6-Dimethyl-undec-2-ene → (S)-4-methylnonanoic acid

HRID 130556Notes

Reaction equation

HRID 130556 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@@H:7]([CH3:13])CCCCC)[CH3:3].C[C:15]([CH3:17])=[O:16].[OH:18]S(O)(=O)=O.O=[Cr](=O)=O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>CC(C)=O>[CH3:1][C@@H:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:13])[CH2:3][CH2:17][C:15]([OH:18])=[O:16]

Participants

5

Reactant 3

HCID 12266711(S)-2,6-Dimethyl-undec-2-eneHCID 45051631Sodium sulphate hydrateHCID 131709961Jones' reagent

Product 1

HCID 6997342(S)-4-methylnonanoic acidYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 162 (7.97 g, 43.7 mmol) was dissolved in acetone (214 mL) and cooled to 0° C. Jones reagent (CrO3/H2SO4) (2.7 M, 95 mL) was added dropwise, and the reaction allowed to warm to room temperature over 18 hours. The reaction was poured on to water/Na2SO4 (200 mL), and the aqueous layer extracted with ethyl acetate (4×100 mL). The combined organics were dried over MgSO4, filtered, and rotovapped to give an oil. The crude oil was chromatographed on silica eluting with hexanes to give 163 as an oil (5.56 g, 74%). 1H NMR (400 MHz, CDCl3) δ 2.40-2.25 (m, 4H), 1.70-1.62 (m, 2H), 1.47-1.11 (m, 8H), 0.87-0.84 (m, 6H); MS APCl m/z 170.9 (M−1, 100%).

Workup

  1. temperatureto warm to room temperature over 18 hours
  2. extractionthe aqueous layer extracted with ethyl acetate (4×100 mL)
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. customto give an oil
  6. customThe crude oil was chromatographed on silica eluting with hexanes

Sources & evidence

ORD record
ord-c725f467599b4576a762dc6966e4c1cc
Source dataset
uspto-grants-2008_06
Patent number
US07381747B2

Reaction notes

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