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

HRID 374733

Reaction equation

HRID 374733 reaction equation
[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]

Participants

9

Reactant 6

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7c15ce39160e47a684f4ef332f3f589b
Source dataset
uspto-grants-1996_01
Patent number
US05482650

Linked notes

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