Vanillin → 3-Methoxy-4-propoxybenzaldehyde
Reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH3:21]>CN(C=O)C.C(OCC)C.[I-].[K+]>[CH2:19]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])[CH2:20][CH3:21]Participants
7
Conditions
- Temperature
- 65 °C
Procedure
To a suspension of vanillin (2.00 g, 13.2 mmol), potassium carbonate (2.74 g, 19.8 mmol) and potassium iodide (60.0 mg, 0.361 mmol) in DMF (15 mL) was slowly added 1-bromopropane (1.56 mL, 17.2 mmol) via syringe. The reaction mixture was stirred at 65° C. for 5 hours. After cooling to room temperature, the mixture was diluted with diethyl ether (100 mL), and the organic phase was washed with water (2×50 mL). After drying over anhydrous MgSO4, filtration and evaporation of the filtrate in vacuo gave crude 4-(propyloxy)-3-methoxybenzaldehyde (2.55 g) which was used in the next step without further purification.
Workup
- temperatureAfter cooling to room temperature
- washthe organic phase was washed with water (2×50 mL)
- dry with materialAfter drying over anhydrous MgSO4, filtration and evaporation of the filtrate in vacuo
Sources & evidence
- ORD record
- ord-7ff25386345e47ae9c2e2339cad0b3a3
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770658B2
Reaction notes
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