Sodium Hydroxide → 3,5-Difluoro-4-(2-propynyloxy)benzoic acid

HRID 2236374Notes

Reaction equation

HRID 2236374 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:16])[C:11]=1[O:12][CH2:13][C:14]#[CH:15])[C:5]([O:7]C)=[O:6].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:16])[C:11]=1[O:12][CH2:13][C:14]#[CH:15])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57445723Methyl 3,5-difluoro-4-(2-propynyloxy)benzoate

Product 1

HCID 574456663,5-Difluoro-4-(2-propynyloxy)benzoic acidYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 30 ml of ethanol were added 5.5 g of methyl 3,5-difluoro-4-(2-propynyloxy)benzoate and 10 ml of 15% aqueous sodium hydroxide solution and the mixture obtained was stirred at room temperature for 2 hours. Then, the reaction mixture was concentrated under reduced pressure. Hydrochloric acid was added to the residue for acidification and then, solid precipitated was collected by filtration to obtain 5.0 g of 3,5-difluoro-4-(2-propynyloxy)benzoic acid represented by the formula:

Workup

  1. customthe mixture obtained
  2. concentrationThen, the reaction mixture was concentrated under reduced pressure
  3. additionHydrochloric acid was added to the residue for acidification
  4. customsolid precipitated
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4da3e0870d40427d96b1a919704a0cfb
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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