Ethylvanillin → 3-Ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8])[CH3:2].Cl.Cl[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[N:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:15][C:16]1[CH:21]=[N:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:7]=[O:8])[CH3:2]Participants
Procedure
To a stirred solution of 3-ethoxy-4-hydroxybenzaldehyde (2.75 g, 16.55 mmol) in acetonitrile (75 mL) was added 5-(chloromethyl)-2-methoxypyridine hydrochloride (3.37 g, 17.38 mmol) and potassium carbonate (9.15 g, 66.20 mmol). The mixture was heated to reflux. After 3 h, the yellow mixture was allowed to cool to room temperature and was diluted with water (400 mL), resulting in the formation of a precipitate. The solids were isolated by filtration and washed with water (50 mL). The filtrate was extracted with chloroform (2×100 mL). The organic phases were combined with the previously isolated solids. The resulting solution was dried over magnesium sulfate, filtered, and concentrated to provide 3.40 g (72%) of 3-ethoxy-4-((6-methoxypyridin-3-yl)methoxy)benzaldehyde as a yellow solid.
Workup
- temperatureThe mixture was heated to reflux
- customresulting in the formation of a precipitate
- customThe solids were isolated by filtration
- washwashed with water (50 mL)
- extractionThe filtrate was extracted with chloroform (2×100 mL)
- dry with materialThe resulting solution was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b975b18faff9477090113d761bf66d87
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174986B2
Reaction notes
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