Sulfuric Acid → Methyl 1-phenylcyclopropane-1-carboxylate

HRID 1282096Notes

Reaction equation

HRID 1282096 reaction equation
[C:1]1([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[C:18](=O)([O-])[O-].[K+].[K+]>CO>[C:1]1([C:7]2([C:10]([O:12][CH3:18])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 802061-Phenylcyclopropanecarboxylic acid

Product 1

HCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-phenylcyclopropanecarboxylic acid (9.8 g) in methanol (121 ml) was added conc. sulfuric acid (0.1 ml) and the mixture was refluxed under heating for 8 hr. The reaction mixture was neutralized by adding an aqueous potassium carbonate solution and concentrated under reduced pressure. The concentrate was extracted with ethyl acetate. The extract was washed with an aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound (8.5 g) as a colorless oil.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 8 hr
  3. concentrationconcentrated under reduced pressure
  4. extractionThe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with an aqueous sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9d77329a76ef4f59a18effc54f9a1633
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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