Hydrochloric Acid → 4-Hexyloxy2,5-dicyanophenol

HRID 1587258

반응식

HRID 1587258 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 542794234-Hexyloxy2,5-dicyanophenol수율 23.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

In a 300 ml-reaction vessel, 35.0 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-hexyloxy-2,5-dicyanophenol (Yield: 22.9%).

후처리

  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

출처 및 근거

ORD 기록
ord-2830346e89174305915ce8e2f2828d89
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05217643

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