Pentaerythritol Tetranitrate → 4-Nitroanisole

HRID 1464889

反応式

HRID 1464889 の反応式
C(C1(CCCCCCCC)C2C=CC=CC=2C2C1=CC=CC=2)CCCCCCC.[C:30]1([O:36][CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH3:38][O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1OC.[CH2:48]1[N:53]([N+:54]([O-:56])=[O:55])[CH2:52][N:51]([N+:57]([O-:59])=[O:58])[CH2:50][N:49]1[N+:60]([O-:62])=[O:61].[CH2:63]([O:80][N+:81]([O-:83])=[O:82])[C:64]([CH2:75][O:76][N+:77]([O-:79])=[O:78])([CH2:70][O:71][N+:72]([O-:74])=[O:73])[CH2:65][O:66][N+:67]([O-:69])=[O:68]>C1COCC1.C(#N)C>[C:30]1([O:36][CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH2:50]1[N:49]([N+:60]([O-:62])=[O:61])[CH2:48][N:53]([N+:54]([O-:56])=[O:55])[CH2:52][N:51]1[N+:57]([O-:59])=[O:58].[CH2:75]([O:76][N+:77]([O-:79])=[O:78])[C:64]([CH2:65][O:66][N+:67]([O-:69])=[O:68])([CH2:63][O:80][N+:81]([O-:83])=[O:82])[CH2:70][O:71][N+:72]([O-:74])=[O:73].[N+:54]([C:43]1[CH:44]=[CH:45][C:40]([O:39][CH3:38])=[CH:41][CH:42]=1)([O-:56])=[O:55]

参加物

11

反応物 5

HCID 6518Pentaerythritol Tetranitrate2 回HCID 7043VeratroleHCID 7519AnisoleHCID 8490Cyclonite2 回HCID 162138639,9-Dioctyl-9H-fluorene3 回

生成物 4

HCID 6518Pentaerythritol TetranitrateHCID 74854-Nitroanisole収率 1%HCID 7519AnisoleHCID 8490Cyclonite

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To probe the scope of the photonitration reaction, the nitration of 9,9-dioctylfluorene, anisole and 1,2-dimethoxybenzene by RDX and PETN was investigated. Extended photolysis (5 h) of a mixture of 9,9-dioctylfluorene and either RDX or PETN in 1:1 acetonitrile:THF at either 254, 313, 334, or 356 nm did not generate any observable products and 9,9-dioctylfluorene was recovered in ca. 90% yield. Photolysis of anisole with RDX or PETN yielded only trace amounts of 4-nitroanisole (<1% GC yield) after 4 hours. Photolysis of 1,2-dimethoxybenzene with either RDX or PETN yielded 1,2-dimethoxy-4-nitrobenzene in only ca. 8% yield after 2 hours; moreover this reaction did not proceed cleanly and numerous polar photoproducts were observed. Based on this set of experiments, anilines were selected as candidates for potential indicators. To create fluorogenic indicators based on the facile nitration reaction between aromatic amines and the photofragmentation products of RDX and PETN, 9,9-disubstituted 9,10-dihydroacridines (DHAs) were targeted as chemosensory.

後処理

  1. customthe scope of the photonitration reaction
  2. customwas recovered in ca. 90% yield

出典と根拠

ORDレコード
ord-119730a219b044019552533df9a4b658
出典データセット
uspto-grants-2015_04
特許番号
US08999722B2

関連ノート

読み込み中…