Ethanol → Ethyl 3-acetylbenzoate

HRID 606505Notes

Reaction equation

HRID 606505 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH2:18][CH3:19])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2203243-Acetylbenzoic acid

Product 1

HCID 11298463Ethyl 3-acetylbenzoateYield 98%

Procedure

A solution of 3-acetylbenzoic acid (4.00 g, 24.366 mmol) and concentrated sulfuric acid (0.078 mL, 1.462 mmol) in ethanol (100 mL) was stirred at 80° C. for 3 days. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to give ethyl 3-acetylbenzoate as a brown powder (4.59 g, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-57084beb65084cebb9526eb1fffb5d55
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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