Water → 4-(4-Chloro-phenyl)-4-methoxy-butyric acid

HRID 1643309Notes

Reaction equation

HRID 1643309 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:13][CH3:14])[CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:13][CH3:14])[CH2:9][CH2:10][C:11]([OH:17])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 595687954-(4-Chloro-phenyl)-4-methoxy-butan-1-olHCID 131709961Jones' reagent

Product 1

HCID 595689054-(4-Chloro-phenyl)-4-methoxy-butyric acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-(4-chloro-phenyl)-4-methoxy-butan-1-ol (120.0 mg, 0.56 mmol) in 6 mL acetone was added dropwise at room temperature 0.6 mL of Jones reagent. After stirring an additional 30 min water was added and the mixture extracted with DCM (3×20 mL). The combined DCM layers were washed with water (2×10 mL) and dried over Na2SO4. The solvent was evaporated under reduce pressure and the crude product was used for the next step without further purification.

Workup

  1. additionwas added
  2. extractionthe mixture extracted with DCM (3×20 mL)
  3. washThe combined DCM layers were washed with water (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-fa4c1596d3944fe78b1fea098cc95e50
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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