Hydrochloric Acid → Methyl 4-chloro-2-hydroxybenzoate

HRID 1423962Notes

Reaction equation

HRID 1423962 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Cl.[C:13]([O-])(O)=O.[Na+]>CO>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787824-Chlorosalicylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-chlorosalicylic acid (16 g, 92.6 mmol) in MeOH (210 mL) was added conc. HCl solution (5 mL). The resultant solution was refluxed for 23 h. After cooled, solid NaHCO3 was added to neutralize the mixture and then was concentrated. The slurry was suspended in EtOAc and filtered through a silica gel plug, washing with EtOAc. The filtrate was washed with ¼ saturated NaHCO3 solution (2×), brine, dried over Na2SO4, filtered and concentrated to provide the title compound (17.2 g). MS ESI(−) m/e: 185.0 (M−1).

Workup

  1. temperatureAfter cooled
  2. concentrationwas concentrated
  3. filtrationfiltered through a silica gel plug
  4. washwashing with EtOAc
  5. washThe filtrate was washed with ¼ saturated NaHCO3 solution (2×), brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e5d4b17047d8486b984892420f468042
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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