Methyl iodide → 7-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

HRID 61684

反応式

HRID 61684 の反応式
COC1C=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:13])[CH2:10]2)=[CH:5][CH:4]=1.[CH3:14]I.[OH-].[K+].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:20][O:21][C:22]1[CH:18]=[C:19]2[C:6]([CH2:11][CH2:10][C:9](=[O:13])[C:8]2([CH3:7])[CH3:14])=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 777857-Methoxy-2-tetralone2 回

生成物 1

HCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒

実験手順

7-Methoxy-3,4-dihydro-1H-naphthalen-2-one (Compound A1, 209 g, 1.18 mol), tetrabutylammonium hydrogen sulfate (40 g, 0.118 mol) and methyl iodide (162 g, 2.60 mol) were suspended in THF (500 ml) at room temperature. Under stirring, the mixture was added with 50% aqueous solution of potassium hydroxide (400 g) over 5 min. Reflux occurred as the inner temperature rapidly increases. Once the inner temperature stopped to increase, stirring was continued for 45 min. The reaction solution was diluted with distilled water (1 L) and extracted twice with CPME (1.5 L). The combined organic layer was washed (distilled water 1 L×3), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was recrystallized with MeOH (1 L) and distilled water (500 ml) to obtain the title compound as a colorless needle-like crystal (177 g, 73%).

後処理

  1. temperatureReflux
  2. temperaturerapidly increases
  3. temperatureto increase
  4. stirringstirring
  5. extractionextracted twice with CPME (1.5 L)
  6. washThe combined organic layer was washed
  7. distillation(distilled water 1 L×3)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting crude product was recrystallized with MeOH (1 L)
  11. distillationdistilled water (500 ml)

出典と根拠

ORDレコード
ord-2eb81a60d2d2494db189c9f1af7b64bc
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

関連ノート

読み込み中…