Sodium Hydroxide → 5-Chloro-2-fluoro-4-methylbenzoic acid

HRID 512046Notes

Reaction equation

HRID 512046 reaction equation
[Cl:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCOCC1.O>[Cl:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58042513Methyl 5-chloro-2-fluoro-4-methylbenzoate

Product 1

HCID 580424465-Chloro-2-fluoro-4-methylbenzoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a stirred solution of methyl 5-chloro-2-fluoro-4-methylbenzoate (Preparation 20, 340 mg, 1.68 mmol) in 12 mL of dioxane/water (5:1) was added aqueous sodium hydroxide (5 M, 1.63 mL, 8.39 mmol). The reaction mixture was stirred at room temperature for 18 hours and then evaporated in vacuo. The resulting residue was suspended in water and extracted with diethyl ether (3×20 mL). The aqueous layer was cooled in an ice bath, acidified with aqueous hydrochloric acid (6 M) and extracted with EtOAc (30 mL). The organic layer was separated, washed with brine (2×20 mL), dried over sodium sulfate, filtered and evaporated in vacuo to yield the title compound as a white solid (266 mg, 84%).

Workup

  1. customevaporated in vacuo
  2. extractionextracted with diethyl ether (3×20 mL)
  3. temperatureThe aqueous layer was cooled in an ice bath
  4. extractionextracted with EtOAc (30 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (2×20 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-6e668867f0c94ae8852011494c5c0954
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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