Water → 5-Ethyl-3-methoxy-4-methoxymethoxy-1-naphthalenecarbaldehyde
Reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([OH:17])=[C:6]([O:15][CH3:16])[CH:7]=[C:8]2[CH:13]=[O:14])[CH3:2].[H-].[Na+].[CH3:20][O:21][CH2:22]Cl.O>CN(C=O)C>[CH2:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([O:17][CH2:20][O:21][CH3:22])=[C:6]([O:15][CH3:16])[CH:7]=[C:8]2[CH:13]=[O:14])[CH3:2]Participants
Procedure
324 g of 5-ethyl-4-hydroxy-3-methoxy-1-naphthalenecarbaldehyde was dissolved in 1 liter of N,N-dimethylformaldehyde, to which 68 g of 60% sodium hydride was gently added under ice-cooling conditions. After agitation for 10 minutes, 128 ml of chloromethyl methyl ether was gradually added so that the reaction temperature did not exceed 15° C. After agitation at room temperature for 20 minutes, the reaction solution was poured into iced water and extracted with ethyl acetate. The resultant organic phase was washed with a saturated saline solution and dried with anhydrous magnesium sulfate. The solvent was distilled off and the resultant residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to obtain 288 g of the captioned compound as a brown oily substance.
Workup
- additionwas gently added under ice-
- temperaturecooling conditions
- customdid not exceed 15° C
- waitAfter agitation at room temperature for 20 minutes
- extractionextracted with ethyl acetate
- washThe resultant organic phase was washed with a saturated saline solution
- dry with materialdried with anhydrous magnesium sulfate
- distillationThe solvent was distilled off
- customthe resultant residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-446b1949d6b7469db01980cc3653b125
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05134111
Reaction notes
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