Ethanol → HCID 86691646, compound

HRID 2204030Notes

Reaction equation

HRID 2204030 reaction equation
[N:1]1([CH:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]CC#N)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-:25].[Na+].[CH3:27][CH2:28][OH:29]>O>[N:1]1([CH:6]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:27][C:28]([OH:25])=[O:29])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86691644HCID 86691644, compound

Product 1

HCID 86691646HCID 86691646, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

13-(1H-imidazol-1-yl)octadecanenitrile (550 mg, 1.66 mmol) was dissolved in EtOH (10 ml) and water (5 ml), to which was then added NaOH (332 mg, 8.30 mmol) and the mixture refluxed for 16 hr. The reaction mixture was then concentrated and acidified with 1N HCl, extracted with DCM, washed with brine solution, dried over MgSO4 and concentrated. The crude product was purified by silica gel column (4% MeOH in DCM) to give 13-(1H-imidazol-1-yl)octadecanoic acid as a thick oil (470 mg, 81%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. extractionextracted with DCM
  3. washwashed with brine solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column (4% MeOH in DCM)

Sources & evidence

ORD record
ord-72edc0755ffd4e3e9d8b216f7567feef
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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