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

HRID 602024Notes

Reaction equation

HRID 602024 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:14])[C:9]=1[O:10][CH2:11][C:12]#[CH:13])[CH:5]=[O:6].ClC1C=CC=C(C(OO)=[O:23])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:14])[C:9]=1[O:10][CH2:11][C:12]#[CH:13])[C:5]([OH:23])=[O:6]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 574456673,5-Difluoro-4-(2-propynyloxy)benzaldehyde

Product 1

HCID 574456663,5-Difluoro-4-(2-propynyloxy)benzoic acidYield 184.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 100 ml of chloroform were added 20 g of 3,5-difluoro-4-(2-propynyloxy)benzaldehyde and 25 g of 3-chloroperbenzoic acid and the mixture obtained was stirred at room temperature for overnight. Then, aqueous sodium sulfite solution was added to the reaction mixture and extracted with chloroform and ethyl acetate in order. The organic layers were combined, dried over magnesium sulfate and concentrated under reduced pressure to obtain 40 g of 3,5-difluoro-4-(2-propynyloxy)benzoic acid.

Workup

  1. customthe mixture obtained
  2. extractionextracted with chloroform and ethyl acetate in order
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6401ec2c109e4ebe9049965cefeb5553
Source dataset
uspto-grants-2011_03
Patent number
US07902400B2

Reaction notes

Loading…