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

HRID 257293

反応式

HRID 257293 の反応式
[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]

参加物

9

反応物 6

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

生成物 1

HCID 189953942,3-Dicyano-4-octyloxyphenol収率 33%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed07586044b3443a807225f3f33b8523
出典データセット
uspto-grants-1993_11
特許番号
US05262082

関連ノート

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