Ethanol → HCID 18920169, compound

HRID 1009469Notes

Reaction equation

HRID 1009469 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:17][CH3:18])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2428284-Fluoro-3-methylbenzoic acid

Product 1

HCID 18920169HCID 18920169, compound

Procedure

5.00 g of 4-fluoro-3-methylbenzoic acid was dissolved in 100 mL of ethanol, and 2.59 mL of concentrated sulfuric acid was added thereto, followed by heating under reflux overnight. The reaction liquid was cooled to room temperature, and then concentrated under reduced pressure, and the obtained residue was alkalified (pH=8) by addition of an aqueous saturated sodium hydrogen carbonate solution under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 5.86 g of ethyl 4-fluoro-3-methylbenzoate.

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight
  3. customThe reaction liquid
  4. concentrationconcentrated under reduced pressure
  5. additionby addition of an aqueous saturated sodium hydrogen carbonate solution under ice-
  6. temperaturecooling
  7. extractionfollowed by extraction with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-90ae230141fa41c69422fc9453029202
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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