Sodium Hydroxide → (+/-)-4-Dodecyl-alpha-phenyl-1H-imidazole-1-acetic acid

HRID 264098Notes

Reaction equation

HRID 264098 reaction equation
[OH-].[Na+].[CH2:3]([C:15]1[N:16]=[CH:17][N:18]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23]CC)=[O:22])[CH:19]=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[N:16]=[CH:17][N:18]([CH:20]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:21]([OH:23])=[O:22])[CH:19]=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 10572975ethyl (+/-)-4-dodecyl-alpha-phenyl-1H-imidazole-1-acetate

Product 1

HCID 10642923(+/-)-4-Dodecyl-alpha-phenyl-1H-imidazole-1-acetic acidYield 60.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid NaOH (0.9 g, 22.6 mmol) was added to a solution of ethyl (±)-4-dodecyl-α-phenyl-1H-imidazole-1-acetate (4.5 g, 11.3 mmol) in 150 mL 95% ethanol. The resulting solution was stirred for 2 hours and then concentrated in vacuo. The residue was partitioned between water and ether, the aqueous layer was acidified with concentrated HCl, and extracted with dichloromethane. The dichloromethane solution was dried over MgSO4, filtered, and concentrated to give a white solid (2.53 g, 55%); mp 110°-118° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and ether
  3. extractionextracted with dichloromethane
  4. dry with materialThe dichloromethane solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0a15367a1beb4881a0dbfe718f901144
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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