2-Hydroxy-p-toluic acid → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

HRID 349688Notes

Reaction equation

HRID 349688 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].[CH:12]1(N=C=NC2CCCCC2)CCCCC1>CO>[CH3:12][O:7][C:6](=[O:8])[C:5]1[C:4](=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=1)[OH:11]

Participants

4

Reactant 2

HCID 57882-Hydroxy-p-toluic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-methylsalicylic acid (75 g, 0.49 mmol) in MeOH (500 mL) at 0° C. was treated with dicyclohexylcarbodiimide (101 g, 0.49 mmol) and the mixture was stirred at room temperature for 2 h. The precipitated dicyclohexylurea was removed by filtration and the filtrate was concentrated in vacuo. The crude residue was purified by distillation (110° C. bath temp, 0.5 mm Hg) to afford 4-methylsalicylic acid methyl ester

Workup

  1. customThe precipitated dicyclohexylurea was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. distillationThe crude residue was purified by distillation (110° C. bath temp, 0.5 mm Hg)

Sources & evidence

ORD record
ord-d3a1b87441e3494b93cf42e35e1c0f4e
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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