Acetic Acid → Benzenemethanol, 2-(dimethylamino)-
Reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:4]=[C:5](CO)[CH:6]=[CH:7][CH:8]=1.C=O.[C:14](O)(=[O:16])C.C([BH3-])#N.[Na+]>C(OCC)(=O)C.O>[CH3:11][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:14][OH:16]Participants
Procedure
In a 250 mL round-bottomed flask, (3-(dimethylamino)phenyl)methanol (1 g) and paraformaldehyde (2.5 g) were added to acetic acid (150 mL) to give a suspension. Sodium cyanoborohydride (2.6 g) was added slowly. The mixture was stirred at room temperature overnight. After concentration of the solvent, water and ethyl acetate (1:1, 100 mL) were added. After separation, the aqueous layer was extracted by ethyl acetate (2×20 mL). The combined organic layers were washed with water (3×50 mL), saturated aqueous NaHCO3 (2×30 mL), and dried over Na2SO4. After filtration and concentration, the residue was taken up into CH2Cl2 and the product was purified by flash chromatography (Varian, Superflash SF40-80 g column), eluting with 0-20% methanol/dichloromethane, to provide the title compound.
Workup
- customto give a suspension
- customAfter separation
- extractionthe aqueous layer was extracted by ethyl acetate (2×20 mL)
- washThe combined organic layers were washed with water (3×50 mL), saturated aqueous NaHCO3 (2×30 mL)
- dry with materialdried over Na2SO4
- filtrationAfter filtration and concentration
- customthe product was purified by flash chromatography (Varian, Superflash SF40-80 g column)
- washeluting with 0-20% methanol/dichloromethane
Sources & evidence
- ORD record
- ord-54344432f25f49ab9b35b459c9a22522
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940737B2
Reaction notes
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