Hydrochloric Acid → 4-Hexyloxy2,5-dicyanophenol

HRID 342325ノート

反応式

HRID 342325 の反応式
[C:1]([C:3]1[CH:9]=[C:8]([OH:10])[C:7]([C:11]#[N:12])=[CH:6][C:4]=1[OH:5])#[N:2].[CH2:13](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.CN(C=O)C>[CH2:13]([O:10][C:8]1[C:7]([C:11]#[N:12])=[CH:6][C:4]([OH:5])=[C:3]([C:1]#[N:2])[CH:9]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 6433912,5-Dihydroxyterephthalonitrile

生成物 1

HCID 542794234-Hexyloxy2,5-dicyanophenol収率 23.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

In a 300 ml-reaction vessel, 350 g (2.19×10-1M) of 2,5-dicyanohydroquinone, 23.8 g (1.44×10-1M) of n-hexylbromide, 20.0 g (1.45×10-1M) of potassium carbonate and 180 ml of DMF were placed, followed by stirring for 3 hours at 120° C. After the reaction, the reaction mixture was cooled and poured into 500 ml of 4N-hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with water and dried with anhydrous magnesium sulfate, followed by distilling-off of the solvent. The resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to obtain 17.6 g of a crude product. The crude product was dissolved in ethanol and treated with activated carbon, followed by recrystallization from ethanol to obtain 8.2 g of 4-hexyloxy2,5-dicyanophenol (Yield: 22.9%).

後処理

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe resultant residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)
  7. customto obtain 17.6 g of a crude product
  8. additiontreated with activated carbon
  9. customfollowed by recrystallization from ethanol

出典と根拠

ORDレコード
ord-6ffb40ec7d9641208bf07915355dfcfd
出典データセット
uspto-grants-1999_01
特許番号
US05858269

反応ノート

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