Potassium Hydroxide → Perylene-3,4-dicarboxylic acid

HRID 266596ノート

反応式

HRID 266596 の反応式
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21]([O:23][C:24](=[O:25])[C:3](=[C:4]23)[CH:2]=1)=[O:22].[OH-:26].[K+]>C(O)(C)(C)C>[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]([C:21]([OH:23])=[O:22])[C:4]3=[C:3]([C:24]([OH:25])=[O:26])[CH:2]=1

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 11759069Perylene-3,4-dicarboxylic anhydride

生成物 1

HCID 21868781Perylene-3,4-dicarboxylic acid収率 50%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

At a yield of 50% in the reaction in the autoclave, monoimide 2b is a suitable starting material for preparing perylene-3,4-dicarboxylic anhydride 4. To this end, 2b is reacted, for example, with KOH in tert-butyl alcohol, followed by hydrolysis to give the monoamide of perylene-3,4-dicarboxylic acid. Acidification of the alkaline solution of the monoamide thus obtained results in further hydrolysis of a portion thereof to give the desired perylene-3,4-dicarboxylic anhydride (4) (while the other portion reverts to the starting material 2b). A particularly suitable acid is 50 per cent acetic acid, which gives yields of more than 60% of 4; based on conversion, the isolated yield of 4 is even more than 90%. The remaining portion of the cyclization product 2b can be separated off without any difficulty by dissolution with hot potassium carbonate solution, filtration and precipitation with acetic acid, so that the anhydride 4 is obtained in high purity.

後処理

  1. customfollowed by hydrolysis

出典と根拠

ORDレコード
ord-156e9896e4ee48958aaa76d1f62500ff
出典データセット
uspto-grants-1997_07
特許番号
US05650513

反応ノート

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