Sodium Chloride → 2-(2,3,4,5-Tetramethoxy-6-methylphenyl)ethanol
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH2:16][CH:17]=[O:18].[BH4-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[C:6]([O:13][CH3:14])=[C:5]([CH3:15])[C:4]=1[CH2:16][CH2:17][OH:18]Participants
Procedure
5.38 g of 2-(2,3,4,5-tetramethoxy-6-methylphenyl)acetaldehyde [prepared as described in step (b)-above] were dissolved in 60 ml of ethanol and reduced using 400 mg of sodium borohydride at 0° C. 150 ml of a saturated aqueous solution of sodium chloride were then added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated to dryness by evaporation under reduced pressure, to give a crude product. This crude product was then purified by column chromatography through silica gel, using a gradient elution method with mixtures of hexane and ethyl acetate ranging from 5:1 to 2:1 by volume as the eluent, to give 5.27 g of the title compound as a colorless oil.
Workup
- customat 0° C
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- concentrationconcentrated to dryness by evaporation under reduced pressure
- customto give a crude product
- customThis crude product was then purified by column chromatography through silica gel
- washa gradient elution method with mixtures of hexane and ethyl acetate ranging from 5:1 to 2:1 by volume as the eluent
Sources & evidence
- ORD record
- ord-28b813f39a2d4eee824b832a8eb6fa1a
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05338855
Reaction notes
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