Cadmium chloride, dihydrate → HCID 178443372, Verbindung

HRID 496990

Reaktionsgleichung

Reaktionsgleichung von HRID 496990
Br[CH:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH3:3].[Cl-].[Cd+2:14].[Cl-]>CCOCC>[CH3:3][CH:2]([Cd:14][CH:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:2][CH3:3])[CH3:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

4

Edukt 2

HCID 24633Cadmium chloride, dihydrateHCID 981602-Bromoundecane

Produkt 1

HCID 178443372HCID 178443372, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Succinic anhydride is opened using methanol (11, step (a)) to give monomethyl succinate (2). This is treated with 2+ equivalents of lithium amide in liquid ammonia (II, step (b)) to form its dianion which is alkylated by the addition of one mole of methyl iodide in ether (II, step (c)) and treatment with ammonium chloride (II, step (d)), giving 2-methylsuccinic acid, 1-methyl ester (3). This is treated with thionyl chloride (II, step (e)) to give the corresponding acid chloride (4). A Grignard reagent is made from 2-bromoundecane and magnesium (II, step (f)) which is treated (II, step (g)) with cadmium chloride to form the corresponding dialkylcadmium, di(2-undecyl)cadmium, (5). The dialkylcadmium reagent (5) is allowed to react with the acid chloride compound (4) (II, step (h)) to form (6) (R=2-undecyl). This is hydrolyzed to the corresponding keto-acid (7) which is reduced either with the Wolff-Kishner or Clemmensen reductions II, step (j)) to give 2,5-dimethyltetradecanoic acid.

Quellen und Nachweise

ORD-Eintrag
ord-482f4431430c4ab6991909fd9c719a9b
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949502B2

Verknüpfte Notizen

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