Benzoic Acid → Ethyl benzoate

HRID 880383Notes

Reaction equation

HRID 880383 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:15](O)[CH3:16]>>[C:1]([O:9][CH2:15][CH3:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 243Benzoic AcidHCID 702EthanolHCID 1118Sulfuric Acid

Product 1

HCID 7165Ethyl benzoate

Procedure

To a flask were added 6.1 g of benzoic acid and 40 ml of anhydrous ethanol, to which 2 ml of concentrated sulfuric acid was added slowly and dropwise with stirring. The mixture was heated under reflux for 6 hours, and then cooled to room temperature. The solvent was distilled under reduced pressure and the residue was diluted with 30 ml of ethyl acetate and 25 ml of water. The aqueous layer was extracted with ethyl acetate (30 ml×2) and the organic layers were combined, washed with saturated sodium bicarbonate solution to neutral and then with saturated NaCl, dried with anhydrous magnesium sulfate, and filtrated. The solvent was distilled under reduced pressure to give ethyl benzoate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. distillationThe solvent was distilled under reduced pressure
  4. additionthe residue was diluted with 30 ml of ethyl acetate and 25 ml of water
  5. extractionThe aqueous layer was extracted with ethyl acetate (30 ml×2)
  6. washwashed with saturated sodium bicarbonate solution to neutral and then with saturated NaCl
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltrated
  9. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-9b8f410f56da474cace3cb0ec51b8564
Source dataset
uspto-grants-2015_03
Patent number
US08993575B2

Reaction notes

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