Citric Acid → HCID 58508845, compound

HRID 454564Notes

Reaction equation

HRID 454564 reaction equation
[OH-].[Na+].C([O:6][C:7]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:28][C:8]=1[C:9]([NH:11][C:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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>[OH:6][C:7]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([CH3:35])[CH3:34])=[CH:28][C:8]=1[C:9]([NH:11][C:12]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][C:13]=1[C:14]([OH:16])=[O:15])=[O:10]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium Hydroxide3×HCID 66990666HCID 66990666, compound

Product 1

HCID 58508845HCID 58508845, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

Dioxane (5.0 mL) and a 4 mol/L aqueous solution of sodium hydroxide (0.20 mL) were added to the obtained methyl 2-(2-acetoxy-5-isopropoxybenzamido)-4-phenylbenzoate (0.072 g), followed by stirring at 50 to 60° C. for 4 hours. The reaction mixture was cooled to room temperature, and a 4 mol/L aqueous solution of sodium hydroxide (0.081 mL) was added thereto, followed by stirring at 55 to 60° C. for 2 hours. The reaction mixture was cooled to room temperature, and a 4 mol/L aqueous solution of sodium hydroxide (0.040 mL) was added thereto, followed by stirring at 60° C. for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and a 10% aqueous solution of citric acid (9 mL) was added thereto. The solid substance was collected by filtration to obtain 0.039 g of 2-(2-hydroxy-5-isopropoxybenzamido)-4-phenylbenzoic acid as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring at 55 to 60° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringby stirring at 60° C. for 1 hour and 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-b0016bd5ba4b45ef8f05bc96681155b7
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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