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

HRID 1675581
Notes
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Reaction equation

HRID 1675581 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 a 15% aqueous sodium hydroxide solution, and the resulting mixture was stirred at 50° C. for 1 hour. Thereafter, the reaction mixture which had been allowed to cool to near room temperature was concentrated under reduced pressure, and hydrochloric acid was added to the residue to make the mixture acidic. The precipitated crystals were collected by filtration, and dried, and 1.8 g of 3,5-difluoro-4-(2-propynyloxy)benzoic acid was obtained.

Workup

  1. temperatureto cool to near room temperature
  2. concentrationwas concentrated under reduced pressure, and hydrochloric acid
  3. additionwas added to the residue
  4. filtrationThe precipitated crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-da3d959e9e4c4f7aa058d4c22fc5dedd
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08003699B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes