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

HRID 1675578Notes

Reaction equation

HRID 1675578 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 a 15% aqueous sodium hydroxide solution, and the resulting mixture was stirred at room temperature for 2 hours. Thereafter, the reaction mixture was concentrated under reduced pressure. Hydrochloric acid was added to the residue to make the mixture acidic, and the precipitated solids were collected by filtration, and 5.0 g of 3,5-difluoro-4-(2-propynyloxy)benzoic acid was obtained.

Workup

  1. concentrationThereafter, the reaction mixture was concentrated under reduced pressure
  2. additionHydrochloric acid was added to the residue
  3. filtrationthe precipitated solids were collected by filtration

Sources & evidence

ORD record
ord-48be77d3face434291fad8583cb3b313
Source dataset
uspto-grants-2011_08
Patent number
US08003699B2

Reaction notes

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