Water → Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate

HRID 857206Notes

Reaction equation

HRID 857206 reaction equation
[Cl:1][CH2:2][CH:3]([OH:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:18])([CH3:17])[C:13]([O:15][CH3:16])=[O:14].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O.O>CC(C)=O.C(O)(C)C>[Cl:1][CH2:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]([CH3:17])([CH3:18])[C:13]([O:15][CH3:16])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21866631Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionateHCID 131709961Jones' reagent2×

Product 1

HCID 21866630Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionateYield 59%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

Methyl 2-(9-chloro-8-hydroxynonyloxy)-2-methylpropionate (31 g) was dissolved in 465 ml of acetone, and 46 ml of Jones reagent prepared by adding 10.2 ml of conc. sulfuric acid and 12 g of chromic (VI) oxide to 45 ml of water was added dropwise with stirring under ice-cooling. After 3-hour-stirring at room temperature, an excess amount of Jones reagent was decomposed by adding isopropyl alcohol, The reaction mixture was poured into ice-cold water, extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=7.5:1) to provide 18.16 g of the objective compound as oil.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringAfter 3-hour-stirring at room temperature
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=7.5:1)

Sources & evidence

ORD record
ord-6f9520d85ddf49179d76a0207eb25df4
Source dataset
uspto-grants-2006_12
Patent number
US07144906B2

Reaction notes

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