Hydrochloric Acid → 2,3-Dicyano-4-octyloxyphenol

HRID 257293

반응식

HRID 257293 반응식
[Na].[C:2]([C:4]1[C:10]([C:11]#[N:12])=[C:9]([OH:13])[CH:8]=[CH:7][C:5]=1[OH:6])#[N:3].[O-]CC.[I-].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].Cl>C(O)C.O>[C:2]([C:4]1[C:10]([C:11]#[N:12])=[C:9]([O:13][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:8]=[CH:7][C:5]=1[OH:6])#[N:3]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 81401-BromooctaneHCID 784672,3-DicyanohydroquinoneHCID 1194401-Hydroxyethyl radicalHCID 5360545Sodium

생성물 1

HCID 189953942,3-Dicyano-4-octyloxyphenol수율 33%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

Sodium (1.15 g, 50 mmoles) was reacted with anhydrous ethanol (200 mL) under a nitrogen atmosphere. 2,3-dicyanohydroquinone (8.01 g, 50 mmoles) in anhydrous ethanol (50 mL) was added dropwise to the ethoxide solution. Upon completion of the addition, potassium iodide (0.5 g) in 5 mL water was added. This solution was brought to reflux and octyl bromide (9.66 g, 50 mmoles) was added dropwise. The reaction was then refluxed under nitrogen atmosphere for one day. The mixture was acidified with 0.5N aqueous HCl and the solvents were removed under reduced pressure. The crude reaction mixture was flash chromatographed using silica gel and methylene chloride as eluent. The appropriate fractions containing the desired product, 2,3-dicyano-4-octyloxyphenol, were combined and the solvent removed under reduced pressure on a rotary evaporator. The crude product was recrystallized from ethanol/water to give 4.5 g 2,3-dicyano-4-octyloxyphenol.

후처리

  1. additionwas added
  2. temperatureto reflux
  3. temperatureThe reaction was then refluxed under nitrogen atmosphere for one day
  4. customthe solvents were removed under reduced pressure
  5. customThe crude reaction mixture
  6. customchromatographed
  7. additionThe appropriate fractions containing the desired product, 2,3-dicyano-4-octyloxyphenol
  8. customthe solvent removed under reduced pressure on a rotary evaporator
  9. customThe crude product was recrystallized from ethanol/water

출처 및 근거

ORD 기록
ord-ed07586044b3443a807225f3f33b8523
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05262082

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