Methanol → Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

HRID 709638Notes

Reaction equation

HRID 709638 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.[CH3:21]O>>[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

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 577059733-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acid

Product 1

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

Procedure

To a solution of 3-cyclopropyl-3-(3-hydroxyphenyl)propanoic acid (longer retention time: 2.47 g) in methanol (60 mL) was added conc. sulfuric acid (64 μL), and the mixture was heated under reflux for 12 hr. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate (30 mL), and washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound (2.53 g) as a colorless oil. This compound was used for the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hr
  3. customthe solvent was evaporated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate (30 mL)
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-849cae8974af43c29705f6971b50abd8
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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