1927
DOI: 10.1002/cber.19270601010
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Über das symmetrische Dichlor‐dimethylsulfat, Chlormethyl‐schwefelsäurechlorid und ähnliche Derivate des Formaldehyds

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Cited by 10 publications
(10 citation statements)
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“…Initially, we examined the known literature procedures , to develop a preliminary knowledge of the key challenges in preparing this molecule, which we hoped to leverage in our development of a more scalable process for the preparation of CMCS. However, all the current processes proved unfavorable for large scale use and little useful information was gained from the processes; the reaction conditions were not suitable for our use, and the reactions produced complex mixtures of products requiring extensive purification.…”
Section: Resultsmentioning
confidence: 99%
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“…Initially, we examined the known literature procedures , to develop a preliminary knowledge of the key challenges in preparing this molecule, which we hoped to leverage in our development of a more scalable process for the preparation of CMCS. However, all the current processes proved unfavorable for large scale use and little useful information was gained from the processes; the reaction conditions were not suitable for our use, and the reactions produced complex mixtures of products requiring extensive purification.…”
Section: Resultsmentioning
confidence: 99%
“…In 1927, Fuch and Katscher reported the first synthesis of CMCS in low yield (30%), through the high temperature (>80 °C) reaction of paraformaldehyde and chlorosulfonic acid. Another early report prepared CMCS from chloromethyl chloroformate and chlorosulfonic acid with modest yield and still requiring high reaction temperatures .…”
Section: Introductionmentioning
confidence: 99%
“…The mixture was stirred at 60 °C for 1 h. After cooling the mixture was concentrated and purified by chromatography over silica gel eluting with cyclohexane:AcOEt 5 : 1 to give the tittle compound (32 mg, quantitative) as a colorless oil. 1 H NMR (300 MHz, CDCl 3 ) δ 4.34-4.06 (m, 6H, OCH 2 CH 3 , H-2), 2.86 (dq, J = 16.8 Hz, 1.5 Hz, 1H, H-4), 2.72 (dq, J = 16.8 Hz, 1.4 Hz, 1H, H-4), 2.21 (s, 3H, COCH 3 ), 2.18 (t, J = 1.5 Hz, 3H, C6-CH 3 ), 1.28 (t, J = 7.2 Hz, 3H, OCH 2 CH 3 ), 1.25 (t, J = 7.2 Hz, 3H, OCH 2 CH 3 ); 13…”
Section: 4-diethyl 2-acetyl-5-methyl-3h-furan-24-dicarboxylate (12)mentioning
confidence: 99%
“…The mixture was stirred at 70 °C for 3 h. After cooling the mixture was concentrated and purified by chromatography over silica gel eluting with cyclohexane:AcOEt 5 : 1 to give the tittle compound (10 mg,) as a colorless oil. 1…”
Section: 5-diacetylheptane-26-dione (38)mentioning
confidence: 99%
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