Citric Acid → HCID 5080667, compound

HRID 454459Notes

Reaction equation

HRID 454459 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[OH:3][C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH3:17])=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 66990971HCID 66990971, compound

Product 1

HCID 5080667HCID 5080667, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 4 mol/L aqueous solution of sodium hydroxide (0.67 mL) was added to a dioxane (3.0 mL) solution of methyl 2-hydroxy-5-propoxybenzoate (0.19 g), followed by stirring at room temperature for 1 hour and 30 minutes and then at 55 to 60° C. for 3 hours. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid (15 mL) was added thereto. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.13 g of 2-hydroxy-5-propoxybenzoic acid as a light yellow solid.

Workup

  1. waitat 55 to 60° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  4. additionwas added to the residue
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. additionHexane was added to the obtained residue
  10. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-e1ce335036564c9a95d374e46f596d66
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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