Water → 4-(4-Fluoro-3-methylphenyl)-4-oxobutanoic acid

HRID 1643276Notes

Reaction equation

HRID 1643276 reaction equation
[O:1]1CC[O:3][CH:2]1[CH2:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([CH3:17])[CH:11]=1)[OH:9].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[CH2:7][CH2:6][C:2]([OH:3])=[O:1])=[CH:11][C:12]=1[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 595688013-(1,3-Dioxolan-2-yl)-1-(4-fluoro-3-methylphenyl)propan-1-olHCID 131709961Jones' reagent

Product 1

HCID 64854434-(4-Fluoro-3-methylphenyl)-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(1,3-dioxolan-2-yl)-1-(4-fluoro-3-methylphenyl)propan-1-ol (1.6 g, 6.7 mmol) in 15 ml acetone was added Jones reagent (1.5 mL) dropwise at room temperature. The mixture was stirred for 30 min. and then 50 mL of water was added before extracting with DCM (3×40 mL). The combined DCM layers were washed with water (2×20 mL) and dried over Na2SO4. The solvent was evaporated under reduce pressure and the crude product used for the next step without further purification.

Workup

  1. extractionbefore extracting with DCM (3×40 mL)
  2. washThe combined DCM layers were washed with water (2×20 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated
  5. customthe crude product used for the next step without further purification

Sources & evidence

ORD record
ord-2b02f97d031a47f3b8c03203b2f61b60
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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