Hydrochloric Acid → Pyrenylketone

HRID 496852

反応式

HRID 496852 の反応式
[CH:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.CO[C:19]1[CH:27]=[C:26](OC)[CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[C:8]1([C:21]([C:20]2[C:19]3[C:27]4=[C:15]5[C:14](=[CH:13][CH:12]=3)[CH:1]=[CH:2][CH:3]=[C:4]5[CH:5]=[CH:6][C:26]4=[CH:25][CH:24]=2)=[O:22])[C:7]2[C:16]3=[C:15]4[C:4](=[CH:5][CH:6]=2)[CH:3]=[CH:2][CH:1]=[C:14]4[CH:13]=[CH:12][C:11]3=[CH:10][CH:9]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 31423PyreneHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 86589552Pyrenylketone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Pyrene (10.1 g; 0.05 mol) and 2,4-dimethoxybenzoyl chloride (10 g; 0.05 mol) were dissolved in 400 ml of anhydrous methylene chloride. Anhydrous aluminium chloride (6.6 g; 0.05 mol) was added to the reaction mixture in small portions over 1 h at 0° C. with intense stirring. The reaction mixture was stirred for another 2 h at 0° C., 2 h at rt and then poured onto a mixture of ice and HCl (500 ml) and transferred into a separating funnel. The organic layer was washed with water (1×500 ml), saturated NaHCO3 (2×500 ml) and saturated NaCl (1×500 ml). The organic fraction was evaporated and recrystallised from toluene to give pyrenylketone as white solid (15.7 g; 86%). Found: C, 82.09; H, 4.81. C25H18O3 (MW 366.41) requires C, 81.95; H, 4.95%. 1H-NMR (CDCl3, d): 8.65-6.45 (m, 12 H, arom.), 3.91 (s, 3H, OCH3), 3.55 (s, 3H, OCH3). Mass-spectrum, MALDI-TOF: 388.89 (MI+Na; 15), 366.89 (100), 203.82 (40). Calculated exact mass for C25H18O3: 366.12559; found 366.12617 [1.6 ppm error].

後処理

  1. customtransferred into a separating funnel
  2. washThe organic layer was washed with water (1×500 ml), saturated NaHCO3 (2×500 ml) and saturated NaCl (1×500 ml)
  3. customThe organic fraction was evaporated
  4. customrecrystallised from toluene

出典と根拠

ORDレコード
ord-5ac6799f365b4e6985e923fe9de2b8ef
出典データセット
uspto-grants-2005_09
特許番号
US06946575B2

関連ノート

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