1914
DOI: 10.1002/cber.19140470150
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Ester der Chromsäure

Abstract: destilliert. Unter 0.13 m m und der Temperatur des Bades von 140° ging das Chlorid ohne Zersetzung iiber und die Dampfe zeigten ungefihr 120O. Ausbeute 57 O/O der Theorie. Zur Analyse wurde nochmnls linter gleichem Druck destilliert. 0.1873 g Sbst.: 0.1105 g dgC1.-0.2500 g Sbst.: 0.1489 g AgCI. CIIHIIOICI t242.55). Ber. CI 14.62. Gcf. CI 14.59, 14.73. Das Chlorid ist ein larbloses 61 von unangenehmem, aber ziemlich schwachem Geruch. Beim Abkiihlen auf-40 bis-50° begann es im Laufe einer Stunde krystallinisch z… Show more

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Cited by 29 publications
(2 citation statements)
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“…The isolation and the structural determination of 21 , 23 and 24 obtained by pyrolysis of the acetate and the formation of β‐patchoulene 21 by dehydration of patchouli alcohol with H 2 SO 4 , I 2 , or H 3 BO 3 , led to the – incorrect – conclusion that patchoulol possessed the tricyclic structure B (Figure ). With structure B in mind, an elegant partial synthesis of patchoulol was designed from (+)‐camphor, via an epoxide of 24 , which was expected to lead to optically active "patchouli alcohol" B but in reality led to the true natural product 33 ! However shortly thereafter, structure 33 was finally and unambiguously assigned to patchoulol on the basis of an X‐ray crystal analysis of the known bright red chromic acid ester . The apparently contradictory results of both the chemical elucidation of the structure of patchoulol and of its partial synthesis from (+)‐camphor were explained in a subsequent article .…”
Section: Analytical Investigations Of Patchouli Essential Oilmentioning
confidence: 98%
“…The isolation and the structural determination of 21 , 23 and 24 obtained by pyrolysis of the acetate and the formation of β‐patchoulene 21 by dehydration of patchouli alcohol with H 2 SO 4 , I 2 , or H 3 BO 3 , led to the – incorrect – conclusion that patchoulol possessed the tricyclic structure B (Figure ). With structure B in mind, an elegant partial synthesis of patchoulol was designed from (+)‐camphor, via an epoxide of 24 , which was expected to lead to optically active "patchouli alcohol" B but in reality led to the true natural product 33 ! However shortly thereafter, structure 33 was finally and unambiguously assigned to patchoulol on the basis of an X‐ray crystal analysis of the known bright red chromic acid ester . The apparently contradictory results of both the chemical elucidation of the structure of patchoulol and of its partial synthesis from (+)‐camphor were explained in a subsequent article .…”
Section: Analytical Investigations Of Patchouli Essential Oilmentioning
confidence: 98%
“…157-158°. The alcohol did not react with chromic acid, nor did it form a chromate under conditions described by Wienhaus (10); it gave no coloration with tetranitromethane and was recovered unchanged after attempted hydrogenation with a platinum oxide catalyst. The melting point and rotation are both higher than those of the isomeric alcohols, ledol, m.p.…”
mentioning
confidence: 90%