Lithium Hydroxide → 2-Chloro-4-methylbenzoic acid

HRID 6970

Reaction equation

HRID 6970 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].[OH-].[Li+]>O1CCCC1.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 tetrahydrofuran (10 mL) methyl alcohol (5 mL) and water (2.5 mL) is added 2N lithium hydroxide (8.12 mL, 16.2 mmol). The reaction mixture is heated at 50° C. for 2.5 hr, cooled to room temperature, and then quenched with 5N hydrochloric acid (3.24 mL). The mixture is concentrated to remove the tetrahydrofuran and methyl alcohol. A white precipitate is formed and is filtered. After drying, 0.922 g (100%) of 2-chloro-4-methylbenzoic acid is isolated. ES(−)MS m/z 169, (M−H)− consistent with 1 Cl.

Workup

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

Sources & evidence

ORD record
ord-cea61636641643349db50d2479857ff0
Source dataset
uspto-grants-2006_08
Patent number
US07084170B2

Linked notes

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