Butanedione → 1-Acetyl-3,5-dimethyl Adamantane

HRID 2302097

Reaktionsgleichung

Reaktionsgleichung von HRID 2302097
ON1C(=O)C2=CC=CC=C2C1=O.CC12CC3CC(CC(C)(C3)C1)C2.C(C(C)=O)(C)=O.[C:31]([C:34]12[CH2:44][C:38]3([CH3:45])[CH2:39][C:40](C)([CH2:42][C:36]([C:46](=O)C)([CH2:37]3)[CH2:35]1)[CH2:41]2)(=[O:33])[CH3:32].[C:49]([C:52]12[CH2:62][C:56]3([CH3:63])[CH2:57][C:58]([OH:61])([CH2:60][C:54](C)([CH2:55]3)[CH2:53]1)[CH2:59]2)(=O)C>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[C:31]([C:34]12[CH2:44][C:38]3([CH3:45])[CH2:39][CH:40]([CH2:42][C:36]([CH3:46])([CH2:37]3)[CH2:35]1)[CH2:41]2)(=[O:33])[CH3:32].[CH3:49][C:52]12[CH2:59][C:58]3([OH:61])[CH2:60][CH:54]([CH2:55][C:56]([CH3:63])([CH2:57]3)[CH2:62]1)[CH2:53]2.[CH3:45][C:38]12[CH2:44][CH:34]3[CH2:41][CH:40]([CH2:42][C:36]([CH3:35])([C:31]3=[O:33])[CH2:37]1)[CH2:39]2

Komponenten

10

Edukt 5

HCID 650ButanedioneHCID 10665N-HydroxyphthalimideHCID 128001,3-Dimethyladamantane2×HCID 121131411,3-Diacetyl-5,7-dimethyladamantaneHCID 134640741-Acetyl-3,5-dimethyl-7-adamantanol

Produkt 3

HCID 2657933,5-Dimethyl-1-adamantanolAusbeute 7 %HCID 121131241-Acetyl-3,5-dimethyl AdamantaneAusbeute 19 %HCID 126443321,3-Dimethyl-4-adamantanoneAusbeute 3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6277Cobalt diacetateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

The procedure of Example 7 was repeated, except that a mixture further comprising 0.3 mmol of N-hydroxyphthalimide in addition to the 1,3-dimethyladamantane, biacetyl, cobalt(II) acetate, and acetic acid was subjected to the reaction. As a result, 1-acetyl-3,5-dimethyladamantane (yield 19%, selectivity 53%), 1,3-diacetyl-5,7-dimethyladamantane (trace), 1-acetyl-3,5-dimethyl-7-adamantanol (trace), 1,3-dimethyl-5-adamantanol (yield 7%, selectivity 19%), and 1,3-dimethyl-4-adamantanone (yield 3%, selectivity 8%) were formed, at a conversion rate from 1,3-dimethyladamantane of 36%.

Aufarbeitung

  1. customwas subjected to the reaction

Quellen und Nachweise

ORD-Eintrag
ord-7dc3b844d7944b67a5ce8404f73c1435
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06429314B1

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