Acetone → 4-[3-(Benzyloxy)-5-(methoxycarbonyl)phenoxy]benzoic acid

HRID 75973Notes

Reaction equation

HRID 75973 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([O:19][C:20]2[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][CH:21]=2)[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:30]>CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.O>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]([CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=1)[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([OH:30])=[O:27])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 86666550HCID 86666550, compound2×

Product 1

HCID 669721544-[3-(Benzyloxy)-5-(methoxycarbonyl)phenoxy]benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 131709961Jones' reagentSolvent

Procedure

To a stirring solution of Methyl 3-(benzyloxy)-5-(4-formylphenoxy)benzoate (30 g) (Intermediate 11) in acetone, Jones reagent was added drop wise at 0° C. until the brown color persists in the reaction mixture. After completion of the reaction mixture was diluted with water and extracted with DCM. All organic layers were combined and washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to get pure white solid (30 g).

Workup

  1. extractionextracted with DCM
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-36ff76e0b25d49b1b46d87d6ecf6651e
Source dataset
uspto-grants-2014_09
Patent number
US08835469B2

Reaction notes

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