Hydrochloric Acid → 6-Cyano-1-carboxy-2-naphthol

HRID 1419243Notes

Reaction equation

HRID 1419243 reaction equation
[OH-].[K+].[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]([O:17]C)=[O:16])=[C:10]([OH:19])[CH:9]=[CH:8]2)#[N:4].Cl>O.CO>[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]([OH:17])=[O:16])=[C:10]([OH:19])[CH:9]=[CH:8]2)#[N:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13439059Methyl 6-cyano-2-hydroxy-1-naphthoate

Product 1

HCID 538463576-Cyano-1-carboxy-2-naphtholYield 65.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution prepared by dissolving 71 g of potassium hydroxide in 1.5 liter of water was added to a solution prepared by dissolving 24.0 g of 6-cyano-1-methoxycarbonyl-2-naphthol in 4.7 liters of methanol, followed by stirring at 50°-60° C. for 24 hours. After cooling, the reaction mixture was made to an acidic solution with addition of 10% hydrochloric acid. The precipitate was collected by filtration and washed with a small amount of water to obtain 14.8 g of the desired product.

Workup

  1. customA solution prepared
  2. additionwas added to a solution
  3. customprepared
  4. temperatureAfter cooling
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with a small amount of water

Sources & evidence

ORD record
ord-6318cf02515f42538d1affbbbd5784d1
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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