1962
DOI: 10.1021/jo01054a022
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Dehydration of Alcohols in Dimethyl Sulfoxide1,2

Abstract: Dehydration of Alcohols 2377 through a Nester-Faust spinning band column to yield 9.0 g. of diethyl methylmalonate (40%), b.p. 43-54°( 0.8 mm), and 11.0 g. of diethyl dichloromethylmethylmalonate (33%), b.p. 73-75°(0.5 mm.). A dark pot residue remained (4.0 g.). The infrared spectrum of the dichloro fraction was identical in all respects to that of the fraction formed in the sodium trichloroacetate run listed above.Reaction of Diethyl Methylsodiomalonate with Bromoform. The reaction was performed as in the chl… Show more

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Cited by 93 publications
(22 citation statements)
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“…IR spectra were recorded on a Hitachi 215 grating IR spectrophotometer. DMSO and other 5.0 g, 0.018 mol) and anhydrous zinc chloride (0.50 g, 0.0037 mol) were dissolved in 10 ml of DMSO and heated for 5 min at 170°C. Into this mixture, trichloroacetic acid (0.50 g, 0.0031 mol) was added carefully.…”
Section: Generalmentioning
confidence: 99%
See 1 more Smart Citation
“…IR spectra were recorded on a Hitachi 215 grating IR spectrophotometer. DMSO and other 5.0 g, 0.018 mol) and anhydrous zinc chloride (0.50 g, 0.0037 mol) were dissolved in 10 ml of DMSO and heated for 5 min at 170°C. Into this mixture, trichloroacetic acid (0.50 g, 0.0031 mol) was added carefully.…”
Section: Generalmentioning
confidence: 99%
“…5 reported the dehydration of IXphenethyl alcohol by prolonged heating in DMSO in the presence of a radical inhibitor. Styrene was obtained in 39% yield after heating for 16hr at 160"C. We tried the method for preparing St-C3-St.…”
Section: Illmentioning
confidence: 99%
“…33 Stirring was continued for 10 min, the phases were separated, the organic phase was water washed and dried over calcium chloride. 33 Stirring was continued for 10 min, the phases were separated, the organic phase was water washed and dried over calcium chloride.…”
Section: 3-dimethyl-55-diphenyl-4-pentenoic Acid Hydrazidementioning
confidence: 99%
“…Reduction of N with lithium aluminum hydride, o r preferably with sodium borohydride, gave hhydroxy-l,6,7, l l btetrahydro-2H-dibenz[cd, hlazulene (V) . Dehydration of this alcohol was accomplished by the elegant method of Traynelis, et al, (3) giving the hydrocarbon (VI) in 96% yield. The 1,llb-position of the double bond was assigned on the basis of the n.m.r.…”
mentioning
confidence: 99%
“…Thomas, R. Otson and J. R. Watson Vol. 3 by Raney Nickel catalyzed hydrogenation, o r , by readily converted to the N-formyl (XVI) and Nlithium aluminum hydride -aluminum chloride recarbethoxy (XVII) derivatives with formicacetic duction (12). Attempts to prepare X N by lithium anhydride (14) and with ethyl chloroformate, realuminum hydride reduction of 10,11dihydro-5H-spectively.…”
mentioning
confidence: 99%