Methanol → 2-(Benzamido)-4-(phenethyloxy)benzoic acid

HRID 1673401Notes

Reaction equation

HRID 1673401 reaction equation
[OH-].[Na+].CO.[C:5]([NH:13][C:14]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[C:5]([NH:13][C:14]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:21]=[CH:20][C:15]=1[C:16]([OH:18])=[O:17])(=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57879365Methyl 2-(benzamido)-4-(phenethyloxy)benzoate

Product 1

HCID 578795342-(Benzamido)-4-(phenethyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.30 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise to a mixed solution of 2 mL of methanol and 2 mL of tetrahydrofuran containing 0.19 g of methyl 2-(benzamido)-4-(phenethyloxy)benzoate while ice-cooled, and stirred at room temperature for 14 hours and 30 minutes. The solvent was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid were added. The organic layer was separated, the solvent was evaporated under reduced pressure and the residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to obtain 85 mg of 2-(benzamido)-4-(phenethyloxy)benzoic acid as white solid.

Workup

  1. temperaturecooled
  2. customThe solvent was evaporated under reduced pressure and ethyl acetate and 1.0 mol/L hydrochloric acid
  3. additionwere added
  4. customThe organic layer was separated
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=2:1]

Sources & evidence

ORD record
ord-d8e128ad00b44890a661b26679f09338
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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