3-Methoxy-4-propoxybenzaldehyde → (3-Methoxy-4-propoxyphenyl)methanol
Reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][CH3:14])[CH2:2][CH3:3]>CCO>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:13][CH3:14])[CH2:2][CH3:3]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Crude 4-(propyloxy)-3-methoxybenzaldehyde (2.55 g) was dissolved in EtOH (30 mL) and cooled to 0° C. NaBH (0.499 g, 13.2 mmol) was added portionwise. After the addition was completed, the ice-water bath was removed and the reaction mixture was stirred at room temperature for 2 hours. Water (50 mL) was added and the resulting mixture was extracted with diethyl ether (3×100 mL). The combined organic layers were dried over anhydrous MgSO4. Removal of the solvent gave a pale yellow oil which was purified by silica gel column chromatography (hexanes/EtOAc, 4:1) to give 4-(propyloxy)-3-methoxybenzyl alcohol (2.38 g, 92% over two steps) as a colorless oil.
Workup
- additionAfter the addition
- customthe ice-water bath was removed
- additionWater (50 mL) was added
- extractionthe resulting mixture was extracted with diethyl ether (3×100 mL)
- dry with materialThe combined organic layers were dried over anhydrous MgSO4
- customRemoval of the solvent
- customgave a pale yellow oil which
- customwas purified by silica gel column chromatography (hexanes/EtOAc, 4:1)
Sources & evidence
- ORD record
- ord-bc11d37b7fc740ffa48b80d5b60597e7
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770658B2
Reaction notes
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