Water → 3,4,5-Trimethoxybenzyl alcohol
Reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14])[CH:8]=[O:9].O>O1CCCC1>[CH3:16][O:15][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([O:4][CH3:3])[C:12]=1[O:13][CH3:14])[CH2:8][OH:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 500 ml round-bottom flask under nitrogen were added 15.32 g (0.41 mol) of sodium borohydride and 100 ml of dry tetrahydrofuran. The mixture was stirred for 10 min., then 20 g (0.108 mol) of 3,4,5-trimethoxybenzaldehyde dissolved in 100 ml of tetrahydrofuran was added dropwise to the solution described above. After stirring at room temperature for 16 hr, the solution was cooled to 0° C., 5 ml of distilled water was added dropwise, and the ice-bath was removed. The mixture was stirred overnight. Tetrahydrofuran was concentrated. The mixture was then diluted with 200 ml of water, and extracted twice with 200 ml of diethyl ether. The extract was dried over magnesium sulfate, concentrated after filtration, and dried in vacuum overnight. 3,4,5-Trimethoxybenzyl alcohol (20.2 g, 100% yield) was obtained as a colorless oil, which can be used without further purification.
Workup
- additionwas added dropwise to the solution
- stirringAfter stirring at room temperature for 16 hr
- customthe ice-bath was removed
- stirringThe mixture was stirred overnight
- concentrationTetrahydrofuran was concentrated
- additionThe mixture was then diluted with 200 ml of water
- extractionextracted twice with 200 ml of diethyl ether
- dry with materialThe extract was dried over magnesium sulfate
- concentrationconcentrated
- filtrationafter filtration
- customdried in vacuum overnight
Sources & evidence
- ORD record
- ord-94db7a3636b04d208cb26797046ef25f
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840991
Reaction notes
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