Ethanol → Benzoic acid, 2-hydroxy-4-methyl-, ethyl ester

HRID 228607

Reaction equation

HRID 228607 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Cl.CN(C)[CH2:15][CH2:16]CN=C=N.O.ON1C2C=CC=CC=2N=N1.C(O)C>CN(C)C=O.O>[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([O:8][CH2:15][CH3:16])=[O:7]

Participants

7

Reactant 4

HCID 702EthanolHCID 57882-Hydroxy-p-toluic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

Product 1

HCID 13013009Benzoic acid, 2-hydroxy-4-methyl-, ethyl esterYield 49%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Methylsalicylic acid (304 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (420 mg), 1-hydroxybenzotriazole hydrate (337 mg), and ethanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 4-methylsalicylate (175 mg, yield 49%).

Workup

  1. customto prepare a solution which
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c7d9c838d6fc4357bcd4712c71a591d2
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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