Citric Acid → HCID 58508801, compound

HRID 454566Notes

Reaction equation

HRID 454566 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:8]=1[C:9]([NH:11][C:12]1[CH:21]=[C:20]([C:22]2[O:23][CH:24]=[CH:25][CH:26]=2)[CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])=[O:10])(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[O:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:20]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:7]=2[OH:6])[CH:21]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 66991505HCID 66991505, compound

Product 1

HCID 58508801HCID 58508801, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
52.5 °C

Procedure

Dioxane (2.0 mL) and a 4 mol/L aqueous solution of sodium hydroxide (0.22 mL) were added to the obtained methyl 2-(2-acetoxy-5-methoxybenzamido)-4-(furan-2-yl)benzoate (0.073 g), followed by stirring at 50 to 55° C. for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and a 10% aqueous solution of citric acid (6 mL) was added thereto. The solid substance was collected by filtration to obtain 0.062 g of 4-(furan-2-yl)-2-(2-hydroxy-5-methoxybenzamido)benzoic acid as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-603ff3e560224ed6bd92d923decba9bf
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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