Lithium Hydroxide → 2-Chloro-4-methylbenzoic acid

HRID 351121

Reaction equation

HRID 351121 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[Li+].[OH-]>C1COCC1.O>[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22019481Methyl 2-chloro-4-methylbenzoate

Product 1

HCID 27357552-Chloro-4-methylbenzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To methyl 2-chloro-4-methylbenzoate (1.00 g, 5.42 mmol) in THF (10 mL) MeOH (5 mL) and H2O (2.5 mL) is added 2N LiOH (8.12 mL, 16.2 mmol). The reaction mixture is heated at 50° C. for 2.5 hr, cooled to room temperature, then quenched with 5N HCl (3.24 mL). The mixture is concentrated to remove the TBF and MeOH. A white precipitate is formed and is filtered. After drying, 0.922 g (100%) of 2-chloro-4-methylbenzoic acid is isolated. ESIMS m/e 169 (M−−1; 35Cl) and 171 (M−−1; 37Cl).

Workup

  1. temperaturecooled to room temperature
  2. customquenched with 5N HCl (3.24 mL)
  3. concentrationThe mixture is concentrated
  4. customto remove the TBF and MeOH
  5. customA white precipitate is formed
  6. filtrationis filtered
  7. customAfter drying

Sources & evidence

ORD record
ord-16269d7e8d644fbea34327e0fb2c6251
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Linked notes

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