Acetic Acid → 2-(4-(Hydroxyimino)cyclohexa-2,5-dien-1-ylidene)-2-phenylacetonitrile

HRID 612347

反応式

HRID 612347 の反応式
[OH-].[K+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O-:14])=O.C(O)(=O)C>CO.O>[OH:14][N:12]=[C:15]1[CH:20]=[CH:19][C:18](=[C:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:10]#[N:11])[CH:17]=[CH:16]1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 7416NitrobenzeneHCID 8794PhenylacetonitrileHCID 14797Potassium Hydroxide

生成物 1

HCID 3468332-(4-(Hydroxyimino)cyclohexa-2,5-dien-1-ylidene)-2-phenylacetonitrile収率 77%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒2 回

反応条件

温度
55 °C

実験手順

60 g of KOH are dissolved in 300 ml of methanol and heated up to 55° C. To the solution are added 32.2 g (0.27 mol) of phenylacetonitrile followed by 30.8 g (0.25 mol) of nitrobenzene. The reaction mixture is stirred at 55° C. for 4 hrs. After cooling, 400 ml of water are added with stirring. The resulting solution is acidified by addition of 110 ml of acetic acid in 100 ml of water, leading to a yellow-orange precipitate. The mixture is then filtered, and the yellow solid is washed with a mixture of methanol and water. The crude product is dried in air, boiled with 150 ml of benzene for 15 min., cooled, filtered and dried under vacuum. 42.6 g (77%) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile are obtained in the form of a yellow solid having a melting point of 159-163° C. (dec.).

後処理

  1. temperatureAfter cooling
  2. stirringwith stirring
  3. filtrationThe mixture is then filtered
  4. washthe yellow solid is washed with a mixture of methanol and water
  5. dry with materialThe crude product is dried in air
  6. waitboiled with 150 ml of benzene for 15 min.
  7. temperaturecooled
  8. filtrationfiltered
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-fb35ee7f28804bd1807b9f0d9e77c306
出典データセット
uspto-grants-1999_12
特許番号
US06004724

関連ノート

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