Ethyl Acetate → 3-(Benzyloxy)propanoic acid

HRID 613357Notes

Reaction equation

HRID 613357 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:15].OS(O)(=O)=O.O=[Cr](=O)=O.C(OCC)(=O)C>CC(C)=O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]([OH:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3479713-Benzyloxy-1-propanolHCID 131709961Jones' reagent

Product 1

HCID 156088133-(Benzyloxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 3-benzyloxy-1-propanol (1.66 g) dissolved in acetone (10 ml) was added 2N Jones reagent (10 ml) while cooling on ice, and the mixture was stirred for 4 hours at room temperature. Ethyl acetate was added, and the resultant mixture was washed with water. The organic layer was extracted with a sat. aq. K2CO3, and the aqueous layer was washed with ethyl acetate. The washed material was acidified with dilute HCl, again extracted with ethyl acetate, then washed with saturated brine. Drying over anhydrous magnesium sulfate and concentrating under reduced pressure yielded 1.27 g of 3-benzyloxypropionic acid as a colorless crystals.

Workup

  1. temperaturewhile cooling on ice
  2. washthe resultant mixture was washed with water
  3. extractionThe organic layer was extracted with a sat. aq. K2CO3
  4. washthe aqueous layer was washed with ethyl acetate
  5. extractionagain extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialDrying over anhydrous magnesium sulfate
  8. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-f91d08302f4b467885812208feee33b0
Source dataset
uspto-grants-1999_12
Patent number
US06008224

Reaction notes

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