Sodium Hydroxide → HCID 86672135, compound

HRID 82313

Reaction equation

HRID 82313 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[N:8]=[N:7]1)C.[OH-].[Na+]>CO.O>[OH2:3].[OH:17][C:13]1[CH:12]=[C:11]([C:9]2[N:8]=[N:7][N:6]([CH2:5][C:4]([OH:18])=[O:3])[CH:10]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70847799Ethyl[4-(3-Hydroxyphenyl)-1H-1,2,3-triazol-1-yl]acetate

Product 1

HCID 86672135HCID 86672135, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl[4-(3-Hydroxyphenyl)-1H-1,2,3-triazol-1-yl]acetate (Preparation 291, 27.2 g, 0.110 mol) was dissolved in methanol (200 mL), and a solution of NaOH (4.84 g, 121 mmol) in water (40 mL) was added. The solution was kept at room temperature for 24 hours. Methanol was evaporated in vacuo, water (120 mL) was added, and the solution was refluxed with activated charcoal. The mixture was filtered, and 11 M HCl was added to the filtrate. The mixture was dissolved by addition of water (120 mL) and cooled to carry out the crystallization. The crystals were filtered, washed with water (2×25 mL), and evaporated to dryness to afford the title compound as brown crystals (mp 186.3-188.7° C.) in 99.0% yield 23.9 g. MS m/z 218 [M−H]−

Workup

  1. customMethanol was evaporated in vacuo, water (120 mL)
  2. additionwas added
  3. temperaturethe solution was refluxed with activated charcoal
  4. filtrationThe mixture was filtered
  5. addition11 M HCl was added to the filtrate
  6. dissolutionThe mixture was dissolved by addition of water (120 mL)
  7. temperaturecooled
  8. customthe crystallization
  9. filtrationThe crystals were filtered
  10. washwashed with water (2×25 mL)
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-8a7dcd844d9f4a55a6a7deb2c767930a
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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