Sodium Hydroxide → 3-Fluoro-4-isopropoxybenzoic acid

HRID 1690164Notes

Reaction equation

HRID 1690164 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])[C:5]([O:7]C(C)C)=[O:6].[OH-].[Na+].[Cl-].[NH4+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[O:14][CH:15]([CH3:17])[CH3:16])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66904979Isopropyl 3-fluoro-4-(1-methylethoxy)benzoate

Product 1

HCID 179028843-Fluoro-4-isopropoxybenzoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Isopropyl 3-fluoro-4-(1-methylethoxy)benzoate (618 mg, 2.57 mmol) was dissolved in methanol (13 mL). The resultant mixture was added with 1N aqueous solution of sodium hydroxide (13 mL) under ice-cold conditions and stirred at 60° C. for 1 hour. The reaction solution was added with a saturated solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. 3-Fluoro-4-(1-methylethoxy)benzoic acid (505 mg, yield 99%) was obtained as a white crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46b8f53f1c51482dac1164ad7f1dcbc5
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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