Hydrochloric Acid → 2,4-Dimethoxybenzoic acid

HRID 501785

Reaction equation

HRID 501785 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].C(Cl)(Cl)Cl.O.Cl>C(O)C.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6212ChloroformHCID 137451Benzoic acid, 2,4-dimethoxy-, methyl ester

Product 1

HCID 70522,4-Dimethoxybenzoic acidYield 91.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
32.5 °C

Procedure

53 g of methyl 2,4-dimethoxybenzoate was dissolved in 160 mL of ethanol, to which 104 mL of a 5M aqueous solution of sodium hydroxide was added, and this mixture was stirred for 2 hours at 25 to 40° C. Then, chloroform and water were added to the reaction mixture, which was adjusted to pH 2 with 6M hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 45 g of 2,4-dimethoxybenzoic acid as white solid.

Workup

  1. additionwas added
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-e242f1be75104dde819827f3f1c9954d
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Linked notes

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