Sulfuric Acid → 2-Naphthyl isopropyl ketone

HRID 1664096ノート

反応式

HRID 1664096 の反応式
[Mg].Br[CH:3]([CH3:5])[CH3:4].[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[C:16]#N.S(=O)(=O)(O)[OH:19]>C(OCC)C>[CH:3]([C:16]([C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1)=[O:19])([CH3:5])[CH3:4]

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 63582-BromopropaneHCID 119442-NaphthalenecarbonitrileHCID 5462224Magnesium

生成物 1

HCID 109654952-Naphthyl isopropyl ketone

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A Grignard reagent prepared by using 0.61 g of magnesium, 3.6 g of 2-bromopropane and 18 ml of anhydrous diethyl ether, was dropwise added to a mixture comprising 3.0 g of 2-naphthonitrile and 20 ml of anhydrous diethyl ether. After completion of the dropwise addition, the mixture was reacted for 12 hours under reflux. The reaction mixture was put into ice water, and 6N sulfuric acid was added to bring the mixture to be weakly acidic, followed by stirring for 0.5 hour. The mixture was extracted with ethyl acetate, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/50) to obtain 1.14 g of 2-naphthyl isopropyl ketone. The NMR spectrum data of this product is as follows.

後処理

  1. additionAfter completion of the dropwise addition
  2. customthe mixture was reacted for 12 hours
  3. temperatureunder reflux
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washby washing with water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/50)

出典と根拠

ORDレコード
ord-8ff6ea1e7cf34634a44f3b6733a6605a
出典データセット
uspto-grants-2011_10
特許番号
US08039420B2

反応ノート

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