Sodium Hydroxide → (+/-)-4-Dodecyl-alpha-phenyl-2H-1,2,3-triazole-2-acetic acid

HRID 2380507Notes

Reaction equation

HRID 2380507 reaction equation
[OH-].[Na+].[CH2:3]([C:15]1[CH:19]=[N:18][N:17]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23]CC)=[O:22])[N:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C>[CH2:3]([C:15]1[CH:19]=[N:18][N:17]([CH:20]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:21]([OH:23])=[O:22])[N:16]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53888023ethyl (+/-)-4-dodecyl-alpha-phenyl-2H-1,2,3-triazole-2-acetate

Product 1

HCID 21469537(+/-)-4-Dodecyl-alpha-phenyl-2H-1,2,3-triazole-2-acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid NaOH (0.44 g, 11 mmol) was added to a solution of ethyl (±)-4-dodecyl-α-phenyl-2H-1,2,3-triazole-2-acetate (2.92 g, 7.3 mmol) in 100 mL 95% ethanol. The resulting yellow solution was stirred for 1 hour and then concentrated in vacuo. The residue was partitioned between water and ether, the aqueous layer was acidified with concentrated HCl and extracted with ethyl acetate. The ethyl acetate solution was dried over MgSO4, filtered, and concentrated to give an off-white solid (2.75 g, quant.); mp 94°-98° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an off-white solid (2.75 g, quant.)

Sources & evidence

ORD record
ord-f6c4b8f73b8c4ea68ac000f1dd5afe4d
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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