Methanol → Methyl 3-cyclopropyl-3-(4-hydroxyphenyl)propanoate

HRID 2101782Notes

Reaction equation

HRID 2101782 reaction equation
[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.[CH3:16]O>S(=O)(=O)(O)O.CCOC(C)=O>[CH:1]1([CH:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:5][C:6]([O:8][CH3:16])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 887MethanolHCID 576725253-Cyclopropyl-3-(4-hydroxyphenyl)propanoic acid

Product 1

HCID 57672485Methyl 3-cyclopropyl-3-(4-hydroxyphenyl)propanoateYield 84%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 21.3 (2.4 g, 12 mmol) in MeOH (25 mL) was added five drops of sulfuric acid. The mixture was stirred overnight at reflux, cooled to room temperature, diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude product was chromatographed on silica gel (0-25% EtOAc/hexane) to afford 21.4 (2.2 g, 84%) as a colorless oil.

Workup

  1. temperatureat reflux
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was chromatographed on silica gel (0-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-a6c8a009d67146f9a794181615e75689
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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