p-Toluenesulfonic acid → HCID 15839203、化合物

HRID 2119426ノート

反応式

HRID 2119426 の反応式
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:10])[C:8]#N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1.[C-:28]#[N:29].[K+]>C1COCC1.O>[OH:24][CH:8]([C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:10])[C:28]#[N:29]

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 9032Potassium CyanideHCID 796772,2-Diphenylpropiononitrile

生成物 1

HCID 15839203HCID 15839203、化合物収率 86.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

42.3 g (0.201 mol of 2,2-diphenylpropionitrile [sic] were dissolved in 230 ml of THF, and 41.4 g (0.217 mol) of p-toluenesulfonic acid were added. Then 14.09 g (0.217 mol) of KCN in 60 ml of water were added dropwise. The mixture was then heated at 40° C. for 3 hours. The reaction mixture was concentrated to about 30% under reduced pressure, taken up in water and extracted three times with ethyl acetate. The combined organic phases were washed twice with sodium disulfite solution, dried with MgSO4 and concentrated under reduced pressure. The crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1). 41.2 g (86%) of 2-hydroxy-3,3-diphenylbutyronitrile were obtained.

後処理

  1. concentrationThe reaction mixture was concentrated to about 30% under reduced pressure
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases were washed twice with sodium disulfite solution
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1)

出典と根拠

ORDレコード
ord-b87f53d694964e8fa907c0c3fecfdb4a
出典データセット
uspto-grants-2004_02
特許番号
US06686369B1

反応ノート

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