3-(9H-Carbazole-9-yl)benzyl alcohol synthesis
- Product Name:3-(9H-Carbazole-9-yl)benzyl alcohol
- CAS Number:71935-22-3
- Molecular formula:C19H15NO
- Molecular Weight:273.33
110677-45-7
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Yield:71935-22-3 91%
Reaction Conditions:
with methanol;sodium tetrahydroborate in tetrahydrofuran at 20; for 1.5 h;
Steps:
1.1.2 4-(9H-carbazol-9-yl)phenyl)methanol (2)
Example 1.1.2
4-(9H-carbazol-9-yl)phenyl)methanol (2)
4-(9H-carbazol-9-yl)benzaldehyde (1) (8.0 g, 29.5 mmol) was dissolved in a (2:1) mixture of tetrahydrofuran/methanol.
Sodium borohydride (1.4 g, 38.3 mmol) was added portion wise to the reaction mixture.
The reaction mixture was stirred for about 1.5 hours at room temperature and the solvents were then removed.
Deionized water was then added to the crude material, and 1M HCl was added dropwise until the solution was neutral.
The material was then extracted with ethyl acetate and washed with water.
The ethyl acetate was then removed and the product 2 was precipitated out of dichloromethane/hexanes to yield white solid 2 (91% yield).
1H NMR (400 MHz, DMSO-d): δ 8.25 (d, J=7.7 Hz, 2H), 7.60 (dd, J1=8.4 Hz, J2=20.2 Hz, 4H), 7.45-7.41 (m, 2H), 7.35 (d, J=8.4 Hz, 2H), 7.28 (t, J=7.0 Hz, 2H), 5.42-5.40 (m, 1H), 4.65 (d, J=5.5 Hz, 2H)
References:
US2013/87772,2013,A1 Location in patent:Paragraph 0078; 0079
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