I have been trying to reduce the carbonyl group in 9H-carbazole-3-carbaldehyde and 9H-carbazole-3-acetyl to alcoholic group, 2 equivalent of sodium borohydride
was added at 0C to the mixture of methnol and 1 equivalent of corresponding aldehyde, the reaction was then refluxed for 30 mins. Unfortunately, the whole carbonyl group is lost and the reaction ended up with only pure carbazole. I would like to know why I lose the carbonyl group instead of reducing it to alcohol? Is there any other ways that would be useful in making carbazole-3- methanol?
Are you sure it's lost? Because reduction like that should convert aldehyde to benzylic alcohol (if you check this by NMR, you should see a pair of 1H around 5-6 ppm, possibly as a doublet; you loose the weak-field 1H, singlet at about 10ppm).
What analytic method did you use to come to this conclusion?
Thanks for your answe, I used both NMR and mass spectrometry to analyza and only show pure carbazol. I am wondering why is that happene?
Did you check source material? Cause if it went bad or was of poor quality, that can be the cause.
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