Water → 4-Methoxybenzaldehyde
Reaction equation
CCN(CC)CC.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.O.C(C1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1)(C)(C)C>ClCCCl>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Complex 8 (8.8 mg, 0.021 mmol) and NEt3 (14 μL, 0.10 mmol) were dissolved in 1,2-dichloroethane (2 mL). The solution was added to a flask containing 4-methoxybenzyl alcohol (140 mg, 1.01 mmol), H2O (91 μL, 5.05 mmol), and a 1,3,5-tri-tert-butylbenzene internal standard (19.2 mg, 0.078 mmol). The flask was equipped with an air condenser and a stir bar and heated at 60° C. for 24 h with stirring (˜700 rpm). The reaction mixture was cooled to room temperature, the solvent removed under vacuum, and the extent of conversion determined by integration of the 1H NMR spectrum against the internal standard. 4-Methoxybenzaldehyde was formed in >98% yield (based on the average of two runs of this type).
Workup
- additionThe solution was added to a flask
- customThe flask was equipped with an air condenser and a stir bar
- temperatureThe reaction mixture was cooled to room temperature
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-382456599fac430aa212b1678c67eb9e
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08519132B2
Reaction notes
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