Methanol → Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate
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.O.[Cl-].[Na+].[CH3:24]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][CH3:24])=[O:7])[CH2:3][CH2:2]1Participants
6
Conditions
- Temperature
- 64 °C
Procedure
To a solution of 3-cyclopropyl-3-(3-hydroxyphenyl)propanoic acid (99.0 g) in methanol (990 mL) was added conc. sulfuric acid (4.71 g), and the mixture was stirred at 64° C. for 2 hr. Water and sodium chloride were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and then saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (84.0 g) as a pale-yellow oil.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
- dry with materialsaturated brine, and dried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-06024ecabf644964b12911c72c5233b1
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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