Methanesulfonic Acid → Methyl 2-hydroxy-6-cyano-1-naphthylacetate

HRID 1419216Notes

Reaction equation

HRID 1419216 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[C:3]=1[CH2:14][C:15]([OH:17])=[O:16].[CH3:18]S(O)(=O)=O>CO>[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[C:3]=1[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 541793092-Hydroxy-6-cyano-1-naphthylacetic acid

Product 1

HCID 54140506Methyl 2-hydroxy-6-cyano-1-naphthylacetateYield 172.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution containing 18.2 g of 2-hydroxy-6-cyano-1-naphthylacetic acid, 250 ml of methanol and 3 g of methanesulfonic acid was stirred at 40° C. to perform dissolution, followed by stirring at room temperature for 2 days. Then, 5 g of active carbon was added, followed by stirring for 30 minutes. Thereafter, the insoluble matter was filtered off and the solvent was distilled off under reduced pressure. To the residue was added 50 ml of 50% hydrous methanol, and then the precipitate was collected by filtration to obtain 13 g of the desired product.

Workup

  1. dissolutiondissolution
  2. stirringby stirring at room temperature for 2 days
  3. additionThen, 5 g of active carbon was added
  4. stirringby stirring for 30 minutes
  5. filtrationThereafter, the insoluble matter was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the residue was added 50 ml of 50% hydrous methanol
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c3fce285ba904292ab37006d50daf807
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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