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

HRID 2236379Notes

Reaction equation

HRID 2236379 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([F:18])[C:13]=1[O:14][CH2:15][C:16]#[CH:17])[C:5]([O:7]CC#C)=[O:6].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([F:18])[C:13]=1[O:14][CH2:15][C:16]#[CH:17])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 593017902-Propynyl 3,5-difluoro-4-(2-propynyloxy)benzoate

Product 1

HCID 574456663,5-Difluoro-4-(2-propynyloxy)benzoic acidYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To 10 ml of ethanol were added 2.2 g of 2-propynyl 3,5-difluoro-4-(2-propynyloxy)benzoate and 6 ml of 15% aqueous sodium hydroxide solution, and the mixture obtained was stirred at 50° C. for 1 hour. Then, the reaction mixture was concentrated under reduced pressure. Hydrochloric acid was added to the residue for acidification. Crystals precipitated were collected by filtration and dried to obtain 1.8 g of 3,5-difluoro-4-(2-propynyloxy)benzoic acid.

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. customCrystals precipitated
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-5dffc07d2e7241dda5a8e539fe88c664
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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