Salicylaldehyde → 2-Undecyloxybenzaldehyde
Reaction equation
[H-].[Na+].[CH:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[OH:6].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CN(C)C=O.CCCCCC>[CH2:22]([O:6][C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[CH:3]=[O:11])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred suspension of sodium hydride (10.0 mmol), which was prewashed with petroleum ether, in sieve dried dimethylformamide (10 ml) was-added dropwise a solution of salicylaldehyde (10.1 mmol) in dimethylformamide (1 ml). To the reaction mixture was then added undecyl bromide (10.0 mmol) and the mixture stirred for 16 hours at ambient temperature under nitrogen. The reaction mixture was taken up in hexane (50 ml) and washed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml). The organic phase was dried over anhydrous magnesium sulfate and charcoal. Evaporation of the volatiles yielded a colorless liquid which was purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant to afford the desired product as an oil.
Workup
- washwashed with 10 percent sodium hydroxide (2×50 ml) and saturated sodium chloride (50 ml)
- dry with materialThe organic phase was dried over anhydrous magnesium sulfate and charcoal
- customEvaporation of the volatiles
- customyielded a colorless liquid which
- customwas purified by flash chromatography over silica gel with 2 percent ethyl acetate in hexane as eluant
Sources & evidence
- ORD record
- ord-83e7eeecb4d14eccbf8d156b24890cff
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05314918
Reaction notes
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