Ethanol → Ethyl 2-(4-(cyclopropanecarbonyl)phenyl)acetate

HRID 2120383Notes

Reaction equation

HRID 2120383 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.[CH2:16](O)[CH3:17]>S(=O)(=O)(O)O>[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:7]=2)=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 702EthanolHCID 1937314-(Cyclopropylcarbonyl)benzeneacetic acid

Product 1

HCID 11218514Ethyl 2-(4-(cyclopropanecarbonyl)phenyl)acetateYield 88%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Dissolve 4-(cyclopropylcarbonyl)benzeneacetic acid in ethanol (150 mL) containing concentrated sulfuric acid (10 drops). Stir 24 hours. Add triethylamine (2 mL) and concentrate the solution. Dissolve the residue in water/ethyl acetate. Wash the organic phase with saturated sodium hydrogen carbonate solution, dry over anhydrous magnesium sulfate and concentrate. Purify by silica gel chromatography (400 mL silica gel, 20% ethyl acetate/heptane as eluent) to give the title compound (7.0 g, 88%).

Workup

  1. concentrationAdd triethylamine (2 mL) and concentrate the solution
  2. dissolutionDissolve the residue in water/ethyl acetate
  3. washWash the organic phase with saturated sodium hydrogen carbonate solution
  4. dry with materialdry over anhydrous magnesium sulfate
  5. concentrationconcentrate
  6. customPurify by silica gel chromatography (400 mL silica gel, 20% ethyl acetate/heptane as eluent)

Sources & evidence

ORD record
ord-5d3510e8d5ef4ba1be0e498cfd5471d7
Source dataset
uspto-grants-2004_02
Patent number
US06689898B2

Reaction notes

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