Hydrochloric Acid → 4-Ethynyl-2-nitrophenol

HRID 2051637Notes

Reaction equation

HRID 2051637 reaction equation
C([O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9](Cl)=[CH:10]C=O)=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17])(=O)C.[OH-].[Na+].Cl.[C]=O>C(O)(=O)C>[C:9]([C:8]1[CH:14]=[CH:15][C:5]([OH:4])=[C:6]([N+:16]([O-:18])=[O:17])[CH:7]=1)#[CH:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 54409372HCID 54409372, compound2×HCID 178418416HCID 178418416, compound

Product 1

HCID 203793924-Ethynyl-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

In the third step of the process (equation 3), 4-acetoxy-3-nitro-β-chlorocinnamaldehyde is added to a solution of sodium hydroxide. The reaction mixture is maintained at 50° to 80° C. for about 15 to 30 minutes and then cooled at 0° C. In the reaction that occurs, the ester group is hydrolyzed, and hydrogen chloride and carbon monoxide are simultaneously eliminated. The mole ratio of sodium hydroxide to 4-acetoxy-3-nitro-β-chlorocinnamaldehyde is usually about 3 to 10:1. The cooled solution is neutralized with glacial acetic acid to give a precipitate which is separated by filtration. The precipitate is then purified to give crystals of 4-ethynyl-2-nitrophenol.

Workup

  1. temperatureThe reaction mixture is maintained at 50° to 80° C. for about 15 to 30 minutes
  2. customIn the reaction
  3. customto give a precipitate which
  4. customis separated by filtration
  5. customThe precipitate is then purified

Sources & evidence

ORD record
ord-cb79e7dcbd2d4a68a3a28c2aa8691579
Source dataset
uspto-grants-1980_01
Patent number
US04181681

Reaction notes

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