Sulfuric Acid → Methyl 2-fluoro-4-methylbenzoate

HRID 1777530Notes

Reaction equation

HRID 1777530 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[C:17](=O)([O-])[O-].[Na+].[Na+]>CO>[F:6][C:7]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:17])=[O:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 27361452-Fluoro-4-methylbenzoic acid

Product 1

HCID 18759805Methyl 2-fluoro-4-methylbenzoateYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sulfuric acid (2 mL) was added to the solution of 2-fluoro-4-methylbenzoic acid (0.848 g; 5.34 mmol) in methanol (30 mL). The mixture was refluxed for 24 hours. After cooling, the solution was made alkaline by addition of an aqueous solution of sodium carbonate, concentrated under reduced pressure in order to remove methanol, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and was concentrated under reduced pressure to give 0.672 g (75%) of methyl 2-fluoro-4-methylbenzoate as a solid.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. temperatureAfter cooling
  3. concentrationconcentrated under reduced pressure in order
  4. customto remove methanol
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-f641833f5d2f419fb6ff2d6cb9b0ad15
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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