HCID 86666550, compound → 4-[3-(Benzyloxy)-5-(methoxycarbonyl)phenoxy]benzoic acid

HRID 2098334Notes

Reaction equation

HRID 2098334 reaction equation
CC(C)=[O:3].OS(O)(=O)=O.O=[Cr](=O)=O.[CH2:14]([O:21][C:22]1[CH:23]=[C:24]([CH:29]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][C:36]([CH:39]=[O:40])=[CH:35][CH:34]=2)[CH:31]=1)[C:25]([O:27][CH3:28])=[O:26])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)=O.O>[CH2:14]([O:21][C:22]1[CH:31]=[C:30]([CH:29]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=1)[O:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([OH:3])=[O:40])=[CH:35][CH:34]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 86666550HCID 86666550, compound2×HCID 131709961Jones' reagent

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Jones reagent (˜60 mL) was added dropwise to a stirring solution of Methyl 3-(benzyloxy)-5-(4-formylphenoxy)benzoate (Intermediate 12) (30 g, 82.9 mmol, 1 equiv.) in acetone (200 mL) at room temperature until a brown color persists. The reaction mixture was diluted with water and extracted several times with dichloromethane. The combined organic extracts was washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated to furnish acid as white solid (30 g).

Workup

  1. extractionextracted several times with dichloromethane
  2. washThe combined organic extracts was washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-99bea5dd78044fd98604322a6e8f10f3
Source dataset
uspto-grants-2013_05
Patent number
US08450494B2

Reaction notes

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