Sulfuric Acid → Methyl 3-fluoro-4-methylbenzoate

HRID 1777534Notes

Reaction equation

HRID 1777534 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:10]([OH:12])=[O:11].[C:17](=O)([O-])[O-].[Na+].[Na+]>CO>[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:10]([O:12][CH3:17])=[O:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 676873-Fluoro-p-toluic acid

Product 1

HCID 18973767Methyl 3-fluoro-4-methylbenzoateYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sulfuric acid (2 mL) was added to the solution of 3-fluoro-4-methylbenzoic acid (0.831 g, 5.23 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 evaporated to give 0.641 g (73%) of methyl 3-fluoro-4-methylbenzoate as an oily residue which was directly used in the next step.

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. customwas evaporated

Sources & evidence

ORD record
ord-351eadd5e5984e669f2a80720fda19ad
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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