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Cadmium chloride, dihydrate → HCID 178443372、化合物

HRID 496990
ノート
印刷プレビュー

反応式

HRID 496990 の反応式
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]
参加物実験手順出典と根拠反応ノート

参加物

4

反応物 2

HCID 24633Cadmium chloride, dihydrateHCID 981602-Bromoundecane

生成物 1

HCID 178443372HCID 178443372、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

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.

出典と根拠

ORDレコード
ord-482f4431430c4ab6991909fd9c719a9b
出典データセット
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06949502B2

反応ノート

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