Hydrochloric Acid → Methyl 4-chloro-2-hydroxybenzoate

HRID 1746236Notes

Reaction equation

HRID 1746236 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 ¼saturated 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 ¼saturated NaHCO3 solution (2×), brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-75fd09c04a14402ca8c6c44635ae73bc
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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