Ethyl vinyl ether → 6-(1-Ethoxy ethoxy)-2-naphthaldehyde
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH:31]([O:33][CH2:34][CH3:35])=[CH2:32]>C(OCC)=C.C(OCC)(=O)C>[CH2:31]([O:33][CH:34]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2)[CH3:35])[CH3:32]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In a 500 mL three neck flask, equipped with a magnetic stirrer, an addition funnel, and a reflux condenser, were charged 25 g of HNAL (0.1462 mol) and 300 mL of ethyl acetate. 6-Hydroxy-2-naphthaldeyde was not completely soluble even after 3 h stirring at room temperature. To this was added 3.30 g of PPTS (0.0131 mol) and the solution mixture was heated to 70° C. At this temperature, 21 g of ethyl vinyl ether (0.2912 mol) was added dropwise and the reaction mixture became homogeneous upon addition of a few drops of ethyl vinyl ether. After completion of ethyl vinyl ether addition, the reaction temperature was lowered to room temperature and the reaction mixture was stirred overnight. The crude product was purified by column chromatography (silica gel, CH2Cl2) to yield 26 g of pure 6-(1-ethoxy ethoxy)-2-naphthaldehyde (yield: 73%).
Workup
- temperaturethe solution mixture was heated to 70° C
- customwas lowered to room temperature
- stirringthe reaction mixture was stirred overnight
- customThe crude product was purified by column chromatography (silica gel, CH2Cl2)
Sources & evidence
- ORD record
- ord-52e4dc49d2484689aa1609eaca172ff8
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07244542B2
Reaction notes
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