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

HRID 1673395Notes

Reaction equation

HRID 1673395 reaction equation
[OH-].[Na+].CO.[C:5]([NH:13][C:14]1[CH:23]=[C:22]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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]([C:24]#[C:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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 57879537Methyl 2-(benzamido)-4-(phenylethynyl)benzoate

Product 1

HCID 578796162-(Benzamido)-4-(phenylethynyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.24 mL of 2.0 mol/L aqueous sodium hydroxide was added dropwise to a mixed solution of 1 mL of methanol and 2 mL of tetrahydrofuran containing 0.13 g of methyl 2-(benzamido)-4-(phenylethynyl)benzoate at room temperature and stirred at the same temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure and water was added and pH was adjusted to pH 4.0 while ice-cooled with 1.0 mol/L hydrochloric acid. A solid substance was separated by filtration to obtain 0.11 g of 2-(benzamido)-4-(phenylethynyl)benzoic acid as white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure and water
  2. additionwas added
  3. temperaturecooled with 1.0 mol/L hydrochloric acid
  4. customA solid substance was separated by filtration

Sources & evidence

ORD record
ord-def9c4afa7814c3b884e04a3781f357c
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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