Methanol → Methyl 2-(4-(cyclopropanecarbonyl)phenyl)acetate

HRID 1840921Notes

Reaction equation

HRID 1840921 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.[CH3:16]O>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][CH3:16])=[O:14])=[CH:8][CH:7]=2)=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 1937314-(Cyclopropylcarbonyl)benzeneacetic acid

Product 1

HCID 12096482Methyl 2-(4-(cyclopropanecarbonyl)phenyl)acetateYield 68%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Dissolve 4-(cyclopropylcarbonyl)benzeneacetic acid in methanol (100 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 (4.6 g, 68%).

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-e56bc8c8812f4ff89f149c0c7f338fcb
Source dataset
uspto-grants-2004_01
Patent number
US06683094B2

Reaction notes

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