Hydrochloric Acid → HCID 58508682, compound

HRID 454627Notes

Reaction equation

HRID 454627 reaction equation
C[O-].[Na+].CO.CO.C([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:36])[NH:19][C:20]2[CH:25]=[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:23]=[CH:22][C:21]=2[C:32]([O:34][CH3:35])=[O:33])=[C:14]([O:37]C(=O)C)[CH:13]=1)(=O)C.Cl>C(OCC)(=O)C>[OH:37][C:14]1[CH:13]=[C:12]([OH:11])[CH:17]=[CH:16][C:15]=1[C:18]([NH:19][C:20]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:22][C:21]=1[C:32]([O:34][CH3:35])=[O:33])=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 23694274Sodium methanolate methanolHCID 70668767HCID 70668767, compound

Product 1

HCID 58508682HCID 58508682, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under ice-cooling, a 28% sodium methoxide-methanol solution (0.34 g) was added to a methanol (3.1 mL) suspension of 4-(2-(methoxycarbonyl)-5-phenylphenylcarbamoyl)-1,3-phenylene diacetate (0.31 g), followed by stirring at room temperature for 1 hour. The reaction mixture was added to 0.5 mol/L hydrochloric acid (20 mL) under ice-cooling, and then ethyl acetate was added thereto. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue to obtain 0.24 g of methyl 2-(2,4-dihydroxybenzamido)-4-phenylbenzoate as a white solid.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooling
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. additionDiisopropyl ether was added to the obtained residue

Sources & evidence

ORD record
ord-2942c7fe0b8442439a425ebb5149c0df
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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