4-Cyanophenol → HCID 13209512, compound

HRID 2083200Notes

Reaction equation

HRID 2083200 reaction equation
[Na].Cl[C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[OH:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1>CO>[C:17]([C:16]1[CH:19]=[CH:20][C:13]([O:12][C:3]2[N:11]=[CH:10][CH:9]=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])=[CH:14][CH:15]=1)#[N:18]

Participants

5

Reactant 3

HCID 130194-CyanophenolHCID 762582-Chloronicotinic acidHCID 5360545Sodium

Product 1

HCID 13209512HCID 13209512, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6.9 g of metallic sodium in 90 ml of methanol are added 24 g of 2-chloronicotinic acid and 18 g of 4-hydroxybenzonitrile. The methanol is distilled off under reduced pressure, 60 ml of nitrobenzene is added, and the mixture is allowed to stand at 180° C to 190° C for 6 hours. After cooling, an aqueous potassium carbonate solution is added to the reaction mixture, and the whole mixture is filtered off. The aqueous layer is separated, washed with ethyl acetate and made acid with hydrochloric acid. The crystalline precipitate is recrystallized from aqueous ethanol to give 18 g of 2-(4-cyanophenoxy)nicotinic acid melting at 198° C to 200° C.

Workup

  1. distillationThe methanol is distilled off under reduced pressure, 60 ml of nitrobenzene
  2. additionis added
  3. temperatureAfter cooling
  4. additionan aqueous potassium carbonate solution is added to the reaction mixture
  5. filtrationthe whole mixture is filtered off
  6. customThe aqueous layer is separated
  7. washwashed with ethyl acetate
  8. customThe crystalline precipitate is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-4e13a6b57a754b528f4d7679076aa1b6
Source dataset
uspto-grants-1978_04
Patent number
US04085111

Reaction notes

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