6-Chloronaphthalen-1-ol → 6-Chloronaphthalene-1,2-dione

HRID 1665266ノート

反応式

HRID 1665266 の反応式
C1(C([O:9]C(C2C=CC=CC=2)=[Se])=[Se])C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25]([OH:29])=[CH:24][CH:23]=[CH:22]2>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[C:24](=[O:9])[CH:23]=[CH:22]2

参加物

4

反応物 2

HCID 132157076-Chloronaphthalen-1-olHCID 86588323O-(benzenecarbonoselenoyl) benzenecarboselenoate

生成物 1

HCID 203740386-Chloronaphthalene-1,2-dione収率 82.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

To a solution of benzeneselenic anhydride (3.18 g, 8.8 mmol) in tetrahydrofuran (30 ml), which had been heated to 70° C. was added a solution of 6-chloro-1-naphthol (1.5 g, 8.4 mmol) in tetrahydrofuran (5 ml). The reaction was maintained at 70° C. for 15 minutes. The mixture was then concentrated under reduced pressure. The residue was suspended in hexanes (100 ml) and filtered. This was repeated 5 times. The residue was dissolved in dichloromethane (100 ml), filtered and concentrated under reduced pressure to afford the product as an orange solid (1.33 g, 82%); 400 MHz 1H NMR (CDCl3) δ: 8.06 (d, J=8.4 Hz, 1H), 7.49 (dd, J=2 and 8.4 Hz, 1H), 7.41-7.38 (m, 2H), 6.50 (d, J=10 Hz, 1H).

後処理

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. filtrationfiltered
  3. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0deb652d776842829d3c78371d60e6d1
出典データセット
uspto-grants-2011_10
特許番号
US08039503B2

反応ノート

読み込み中…