Water → HCID 59214195, compound

HRID 552829Notes

Reaction equation

HRID 552829 reaction equation
F[CH:2](F)[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:6]#N.S(=O)(=O)(O)[OH:20].[OH-:24].[Na+].[OH2:26]>>[CH:2]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:6]([OH:20])=[O:26])=[O:24]

Participants

5

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 59214383HCID 59214383, compound

Product 1

HCID 59214195HCID 59214195, compound

Procedure

To 3-(difluoromethyl)-4-(2,2,2-trifluoro-1-methylethoxy)benzonitrile (234 mg) were added water (2 ml) and sulfuric acid (2 ml), followed by reflux for 24 hours. After cooling to room temperature, the reaction solution was alkalified with a 5M aqueous NaOH solution, and extracted with diethyl ether (30 ml). The aqueous layer was acidified by 1M HCl, and extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:CH3OH=97:3 to 90:10) to obtain 3-formyl-4-(2,2,2-trifluoro-1-methylethoxy)benzoic acid (151 mg) as a white solid.

Workup

  1. temperatureby reflux for 24 hours
  2. extractionextracted with diethyl ether (30 ml)
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=97:3 to 90:10)

Sources & evidence

ORD record
ord-2bf0538f831d466d976a14c34ba332ca
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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