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

HRID 2236376Notes

Reaction equation

HRID 2236376 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 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-7b8b1b17338f4faf9d83cd0183fc1a7e
Source dataset
uspto-grants-2010_05
Patent number
US07714168B2

Reaction notes

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