Methanol → Methyl Ferulate
Reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5](/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[O:13][CH3:14].S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][O:9][C:8](=[O:10])/[CH:7]=[CH:6]/[C:5]1[CH:11]=[CH:12][C:2]([OH:1])=[C:3]([O:13][CH3:14])[CH:4]=1Participants
Procedure
25 g (0.13 mmol) of (E)-4-hydroxy-3-methoxycinnamic acid was dissolved in 180 ml of methanol, and 5 ml of concentrated sulfuric acid was added thereto. The solution was heated at reflux for 2 hours. The majority of the methanol (about 150 ml) was removed by distillation and the remaining residue was poured into 500 ml of ice-water thereby to effect precipitation of the ester, which was then purified by suction filtration and washed firstly with cold water, then with a small amount of cold saturated sodium bicarbonate solution and finally with cold water and dried at 50° C. under a water-jet vacuum. The product was then purified by chromatography using silica gel (250 g) using dichloromethane:diethyl ether (19:1) as eluant to give 21.78 g of (E)-4-hydroxy-3-methoxycinnamic acid methyl ester in the form of a light-yellow oil.
Workup
- temperatureThe solution was heated
- temperatureat reflux for 2 hours
- customThe majority of the methanol (about 150 ml) was removed by distillation
- additionthe remaining residue was poured into 500 ml of ice-water
- customprecipitation of the ester, which
- filtrationwas then purified by suction filtration
- washwashed firstly with cold water
- dry with materialwith a small amount of cold saturated sodium bicarbonate solution and finally with cold water and dried at 50° C. under a water-jet vacuum
- customThe product was then purified by chromatography
Sources & evidence
- ORD record
- ord-72cf3d046b724e7c887938a390d7968b
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06833421B1
Reaction notes
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