Ethanol → HCID 22955954, compound

HRID 512043Notes

Reaction equation

HRID 512043 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([O:6][CH2:18][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 136574512,5-Difluoro-4-methylbenzoic acid

Product 1

HCID 22955954HCID 22955954, compoundYield 95%

Procedure

To a solution of 2,5-difluoro-4-methylbenzoic acid (5 g, 2.904 mmol) in ethanol (100 mL) was added concentrated sulfuric acid (1 mL). The reaction mixture was stirred at reflux for 18 hours. LCMS showed complete consumption of starting material, so the solvents were removed in vacuo and the resulting residue redissolved in EtOAc (50 mL), and washed with saturated aqueous sodium bicarbonate. The organic layer was separated, and the aqueous layer extracted with EtOAc (2×50 mL). The combined organics were dried over sodium sulfate and evaporated to yield the title compound as a pale yellow oil (5.502 g, 95%).

Workup

  1. temperatureat reflux for 18 hours
  2. customconsumption of starting material
  3. customso the solvents were removed in vacuo
  4. dissolutionthe resulting residue redissolved in EtOAc (50 mL)
  5. washwashed with saturated aqueous sodium bicarbonate
  6. customThe organic layer was separated
  7. extractionthe aqueous layer extracted with EtOAc (2×50 mL)
  8. dry with materialThe combined organics were dried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-abaed093d29d477ba3963d7f1a4923c6
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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