Acetone → 4-Methoxycinnamate methyl ester
Reaction equation
O[C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7]C(O)=O)=[CH:4][CH:3]=1.[C:13](=[O:16])([O-])[O-:14].[K+].[K+].S([O:24][CH3:25])(OC)(=O)=O.[CH3:26]C(C)=O>>[CH3:26][O:14][C:13](=[O:16])[CH:7]=[CH:6][C:5]1[CH:11]=[CH:12][C:2]([O:24][CH3:25])=[CH:3][CH:4]=1Participants
Procedure
p-Hydroxycinnamic acid (10.0 g, 61 mmol) was dissolved in 200 mL of acetone. Potassium carbonate (58.7 g, 213 mmol) was added at room temperature. After 15 mins, dimethyl sulfate (16.4 mL, 213 mmol) was added at room temperature under Argon and then heated under reflux under an Argon atmosphere for 8 hours. The solid was filtered off and then 50 mL of water was added to the filtrates. The solvent was evaporated under reduced pressure and the mixture was extracted two times with 200 mL of ethyl acetate. The combined organic layer was dried over sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/10) to obtain methyl-4-methoxycinnamate [832-01-9] (11.7 g, 99% yield).
Workup
- temperatureheated
- temperatureunder reflux under an Argon atmosphere for 8 hours
- filtrationThe solid was filtered off
- addition50 mL of water was added to the filtrates
- customThe solvent was evaporated under reduced pressure
- extractionthe mixture was extracted two times with 200 mL of ethyl acetate
- dry with materialThe combined organic layer was dried over sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/10)
Sources & evidence
- ORD record
- ord-b83289840dc74be5b45e2c4a6b4b26bf
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07705040B2
Reaction notes
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