Maleic Anhydride → Levopimaric acid

HRID 1911797

反応式

HRID 1911797 の反応式
C1C=CC(/C=C/CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC=1.[CH3:22][CH:23]([C:25]1[CH2:34][CH2:33][C@H:32]2[C:27](=[CH:28][CH2:29][C@H:30]3[C@@:38]([C:40]([OH:42])=[O:41])([CH3:39])[CH2:37][CH2:36][CH2:35][C@@:31]32[CH3:43])[CH:26]=1)[CH3:24].C1(=O)OC(=O)C=C1>C(O)(=O)C>[CH3:24][CH:23]([C:25]1[CH:26]=[C:27]2[CH2:28][CH2:29][C@H:30]3[C@@:38]([C:40]([OH:42])=[O:41])([CH3:39])[CH2:37][CH2:36][CH2:35][C@:31]3([CH3:43])[C@H:32]2[CH2:33][CH:34]=1)[CH3:22]

参加物

5

反応条件

温度
120 °C

実験手順

Example 1 describes the preparation of quaternary ammonium-containing rosin acids and rosin esters, according to the exemplary method shown in FIG. 1. The synthesis for the integration of quaternary ammonium group into the moiety of rosin is described as follows: The abietic acid, maleic anhydride and acetic acid were mixed in a round bottom flask under a nitrogen atmosphere and heated at 120° C. for 12 h to yield levopimaric acid. The levopimaric acid is stirred with dimethylethylenediamine at 85° C. for 8 h, yielding a rosin-derived tertiary ammonium derivative, which is then stirred with an alkyl halide (e.g. bromoethane, bromohexane, bromooctane and bromododecane) at 40° C. in tetrahydrofuran for 48 h to yield quaternary ammonium-containing rosin acid 1. The quaternary ammonium-containing rosin acid is dissolved in thionyl chloride and refluxed for 12 h. Then, thionyl chloride is removed by reduced pressure distillation. Ethanol, triethylamine and tetrahydrofuran are added and stirred at room temperature for 24 h to yield the ethyl ester of quaternary ammonium-containing rosin acid 2.

出典と根拠

ORDレコード
ord-e475057069414be597e7e3bf76c9aa8a
出典データセット
uspto-grants-2013_12
特許番号
US08604128B2

関連ノート

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