Sulfuric Acid → 1-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile

HRID 462278

反応式

HRID 462278 の反応式
C([CH:5]1[CH2:10][C:9]([C:18]#[N:19])([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:20])(OC)=O.S(=O)(=O)(O)O>C(O)(=O)C>[C:18]([C:9]1([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH2:10][CH2:5][C:6](=[O:20])[CH2:7][CH2:8]1)#[N:19]

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 12230235Methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexanecarboxylate

生成物 1

HCID 918051-(4-Fluorophenyl)-4-oxocyclohexanecarbonitrile収率 67%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A reaction mixture consisting of 33.9 gm. (0.123 mole) of 2-carbomethoxy-4-cyano-4-(p-fluorophenyl)cyclohexanone (prepared in Part B, above), 900 ml. glacial acetic acid, and 450 ml. 10% aqueous sulfuric acid is heated with stirring on a steam bath for 24 hours. After allowing the reaction mixture to cool, it is diluted with 2000 ml. water and extracted thoroughly with benzene. The benzene extracts are combined and washed successively with water, with aqueous sodium bicarbonate, and finally with brine. The benzene is then removed by evaporation under reduced pressure, and the solid residue thus obtained is recrystallized from diethyl ether to afford 16.23 gm. (67% yield) of 4-cyano-4-(p-fluorophenyl)cyclohexanone having a melting point at 84° to 88° C.

後処理

  1. temperatureto cool
  2. additionit is diluted with 2000 ml
  3. extractionwater and extracted thoroughly with benzene
  4. washwashed successively with water, with aqueous sodium bicarbonate
  5. customThe benzene is then removed by evaporation under reduced pressure
  6. customthe solid residue thus obtained
  7. customis recrystallized from diethyl ether
  8. customto afford 16.23 gm

出典と根拠

ORDレコード
ord-4d7e11105d8f47409fb7e8b110241c34
出典データセット
uspto-grants-1977_12
特許番号
US04065573

関連ノート

読み込み中…