Sulfuric Acid → Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

HRID 709647Notes

Reaction equation

HRID 709647 reaction equation
[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.S(=O)(=O)(O)O.[C:21](=O)([O-])O.[Na+]>CO>[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)[CH2:5][C:6]([O:8][CH3:21])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 577059733-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acid

Product 1

HCID 57706598Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-cyclopropyl-3-(3-hydroxyphenyl)propanoic acid (1.45 g) in methanol (20 mL) was added conc. sulfuric acid (75 μL), and the mixture was heated under reflux for 14 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound (1.43 g) as a pale-brown oil. This compound was used for the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e3d07eaa595344bdac7fe6d9f527fd20
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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