Sodium Hydroxide → 2-Hydroxy-2-methyl-1-[4-(methylthio)phenyl]-1-butanone

HRID 565123

反応式

HRID 565123 の反応式
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH:10]([CH3:13])[CH2:11][CH3:12])=[CH:5][CH:4]=1.[OH-:15].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[OH:15][C:10]([CH3:13])([CH2:11][CH3:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1)=[O:14]

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 154806432-Methyl-1-[4-(methylthio)phenyl]-1-butanone

生成物 1

HCID 101307312-Hydroxy-2-methyl-1-[4-(methylthio)phenyl]-1-butanone

試薬・触媒・溶媒 3

HCID 21218Trioctylmethylammonium chloride触媒HCID 1140Toluene溶媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a mixture of the ketone from Step 1 (10 g, 48 mmol) and Aliquat® 336 (20 mL) in CCl4 (40 mL) and toluene (80 mL) at r.t. was added NaOH pellets (3.8 g, 96 mmol). While stirring vigourously, the mixture was heated briefly to reflux and was then stirred overnight at r.t. After partitioning between CH2Cl2 and H2O, the whole was filtered through celite. The organic layer was dried (MgSO4), filtered, and evaporated. The residue was purified by flash chromatography (1:10 EtOAc: hexane) to give the title compound as a syrup (5.5 g).

後処理

  1. temperaturethe mixture was heated briefly
  2. temperatureto reflux
  3. stirringwas then stirred overnight at r.t
  4. customAfter partitioning between CH2Cl2 and H2O
  5. filtrationthe whole was filtered through celite
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (1:10 EtOAc: hexane)

出典と根拠

ORDレコード
ord-95d67e736c114d7395561c7f451c366d
出典データセット
uspto-grants-2001_01
特許番号
US06169188A

関連ノート

読み込み中…