Hydrochloric Acid → Methyl 2-(benzamido)-4-hydroxybenzoate

HRID 1673352Notes

Reaction equation

HRID 1673352 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C1(C)C=CC=CC=1.[C:12]([NH:20][C:21]1[CH:30]=[C:29]([O:31]C)[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(OCC)(=O)C>[C:12]([NH:20][C:21]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6451240Aluminum(III) ChlorideHCID 57879519Methyl 2-(benzamido)-4-methoxybenzoate

Product 1

HCID 57879368Methyl 2-(benzamido)-4-hydroxybenzoateYield 36.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

0.94 g of aluminum chloride was added to 7 mL of toluene solution containing 0.67 g of methyl 2-(benzamido)-4-methoxybenzoate at room temperature and stirred at 80° C. for 2 hours and 30 minutes. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid were added and a solid substance was separated by filtration to obtain 0.23 g of methyl 2-(benzamido)-4-hydroxybenzoate as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-512d32b75cf64791a1c5d1d76626eb2c
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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