Production of Benzyl Chloride by Chloromethylation of Benzene. Laboratory and Pilot Plant Studies

Whitmore, Frank C.; Ginsburg, Abram; Rueggeberg, Walter H. C.; Tharp, I. D.; Nottorf, H. A.; Cannon, M.B.; Carnahan, F. L.; Cryder, D.; Fleming, Geo. H.; Goldberg, G. M.; Haggard, Howard W.; Herr, C. H.; Hoover, Troy E.; Lovell, Heather; Mraz, R.; Noll, Clarence I.; Oakwood, Thomas S.; Patterson, H.T.; Strien, R. Van; Walter, Richard W.; Zook, Harry D.; Wagner, Romeo B.; Weisgerber, C. A.; Wilkins, John D.

doi:10.1021/ie50437a013

Cited by 5 publications

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“…In present investigation, we have synthesized the hydroxy methyl derivative (Fig. 2, Compound 2) of Nos using paraformaldehyde (40% formalin solution) and dry HCl gas via Blanc reaction 26 . The excess amount of concentrated HCl or longer reaction time was avoided in order to protect the product from hydrolysis.…”

Section: Resultsmentioning

confidence: 99%

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Biological Evaluation of Noscapine analogues as Potent and Microtubule-Targeted Anticancer Agents

Tomar

Kumar

Tomar

et al. 2019

Sci Rep

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In present investigation, an attempt was undertaken to modify the C-9 position of noscapine (Nos), an opium alkaloid to yield 9 -hydroxy methyl and 9 -carbaldehyde oxime analogues for augmenting anticancer potential. The synthesis of 9-hydroxy methyl analogue of Nos was carried out by Blanc reaction and 9-carbaldehyde oxime was engineered by oxime formation method and characterized using FT-IR, 1H NMR, 13C NMR, mass spectroscopy, and so on techniques. In silico docking techniques informed that 9-hydroxy methyl and 9-carbaldehyde oxime analogues of Nos had higher binding energy score as compared to Nos. The IC50 of Nos was estimated to be 46.8 µM signficantly (P < 0.05) higher than 8.2 µM of 9-carbaldehyde oxime and 4.6 µM of 9-hydroxy methyl analogue of Nos in U87, human glioblastoma cells. Moreover, there was significant (P < 0.05) difference between the IC50 of 9-carbaldehyde oxime and 9-hydroxy methyl analogue of Nos. Consistent to in vitro cytotoxicity data, 9-hydroxy methyl analogue of Nos induced significantly (P < 0.05) higher degree of apoptosis of 84.6% in U87 cells as compared to 78.5% and 64.3% demonstrated by 9-carbaldehyde oxime and Nos, respectively. Thus the higher therapeutic efficacy of 9-hydroxy methyl analogue of Nos may be credited to higher solubility and inhibitory constant (K).

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Section: Resultsmentioning

confidence: 99%

“…The synthesis of 9-hydroxy methyl analogue of Nos was carried out by Blanc reaction 26 . In brief, Nos ( Compound 1 ) (0.413 g, 1 mM) was dissolved in concentrated HCl (5 ml) and then 40% formalin solution (5 ml) was added.…”

Section: Methodsmentioning

confidence: 99%