Hydrochloric Acid → Methyl 2-hydroxy-5-methoxybenzoate

HRID 364177

Reaction equation

HRID 364177 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1.Cl.[C:14](=O)([O-])[O-].[K+].[K+]>CO>[OH:12][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:7]=1[C:8]([O:10][CH3:14])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 757875-Methoxysalicylic Acid

Product 1

HCID 4072341Methyl 2-hydroxy-5-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 73 g of 5-methoxysalicylic acid, and 95 ml of concentrated hydrochloric acid in 700 ml of methanol was heated under reflux for 48 hours. Potassium carbonate (10 g) was added, and the mixture concentrated to an oily residue which was dissolved in 250 ml of ethyl acetate. This solution was washed with two 100 ml portions of 10% sodium bicarbonate solution, then dried over anhydrous sodium sulfate. Evaporation of solvent afforded the title compound as an amber oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. concentrationthe mixture concentrated to an oily residue which
  4. dissolutionwas dissolved in 250 ml of ethyl acetate
  5. washThis solution was washed with two 100 ml portions of 10% sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-0ef4e80abcb3449089c81a09e19d98f1
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Linked notes

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