Hydrochloric Acid → 2-Chloro-6-hydroxybenzoic acid

HRID 1946295Notes

Reaction equation

HRID 1946295 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11]COC)[C:3]=1[C:4]([OH:6])=[O:5].Cl>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 595478622-Chloro-6-(methoxymethoxy)benzoic acid

Product 1

HCID 925912-Chloro-6-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-6-{[(methyloxy)methyl]oxy}benzoic acid (for a preparation see Intermediate 4)(2 g, 9.23 mmol) in THF (20 ml) was added 6 M aqueous HCl (20 ml, 120 mmol). The solution was stirred at ambient temperature for 3 h. The solution was partitioned between ethyl acetate (150 ml) and water (30 ml). The phases were separated and the organic extract washed with water (25 ml). The organic extract was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as a white solid (1.54 g); LCMS: (System 1) (M-H)−=171, tRET=3.26 min.

Workup

  1. customThe solution was partitioned between ethyl acetate (150 ml) and water (30 ml)
  2. customThe phases were separated
  3. extractionthe organic extract
  4. washwashed with water (25 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7f3001ee43144bf4be0e1fb92e766362
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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