Methanol → 2-(Benzamido)-4-(3-phenylpropoxy)benzoic acid

HRID 1673403Notes

Reaction equation

HRID 1673403 reaction equation
[OH-].[Na+].CO.[C:5]([NH:13][C:14]1[CH:23]=[C:22]([O:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=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 Hydroxide2×HCID 57879320Methyl 2-(benzamido)-4-(3-phenylpropoxy)benzoate

Product 1

HCID 578795332-(Benzamido)-4-(3-phenylpropoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.090 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise to a mixed solution of 1 mL of methanol and 1 mL of tetrahydrofuran containing 45 mg of methyl 2-(benzamido)-4-(3-phenylpropoxy)benzoate while ice-cooled and stirred at room temperature for 14 hours and 30 minutes. 0.15 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise and stirred at the same temperature for 5 hours and 30 minutes. The solvent was evaporated under reduced pressure and water was added and pH was adjusted to pH 4.0 with 1.0 mol/L hydrochloric acid. A solid substance was separated by filtration to obtain 32 mg of 2-(benzamido)-4-(3-phenylpropoxy)benzoic acid as white solid.

Workup

  1. temperaturecooled
  2. stirringstirred at the same temperature for 5 hours and 30 minutes
  3. customThe solvent was evaporated under reduced pressure and water
  4. additionwas added
  5. customA solid substance was separated by filtration

Sources & evidence

ORD record
ord-ef7ecd7a4eb141d9999364daeca5b15b
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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