Sodium Sulfite → 4-(Benzyloxy)pentanoic Acid

HRID 883215Notes

Reaction equation

HRID 883215 reaction equation
[CH2:1]([O:8][CH:9]([CH3:14])[CH2:10][CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O.S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[CH2:1]([O:8][CH:9]([CH3:14])[CH2:10][CH2:11][C:12]([OH:17])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 109104254-(Benzyloxy)pentan-1-olHCID 131709961Jones' reagent

Product 1

HCID 577812604-(Benzyloxy)pentanoic AcidYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(benzyloxy)pentan-1-ol (350 mg, 1.80 mmol) in acetone (20 mL) was added Jones reagent (1.9M, 1.9 mL, 3.6 mmol) under ice-cooling, and the mixture was stirred for 30 min. Sodium sulfite was added to the reaction solution, and the solvent was evaporated under reduced pressure. The residual aqueous solution was washed with ethyl acetate, acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→40/60) to give the title compound (236 mg, yield 63%).

Workup

  1. temperaturecooling
  2. customthe solvent was evaporated under reduced pressure
  3. washThe residual aqueous solution was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→40/60)

Sources & evidence

ORD record
ord-782bb4b22e1a4e70a11ab6ccfb2587e5
Source dataset
uspto-grants-2012_08
Patent number
US08236837B2

Reaction notes

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