10-(1H-imidazol-1-yl)octadecan-1-ol → 10-(1H-imidazol-1-yl)octadecanoic acid

HRID 2204040Notes

Reaction equation

HRID 2204040 reaction equation
[N:1]1([CH:6]([CH2:17][CH2:18][CH2:19][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][OH:16])[CH:5]=[CH:4][N:3]=[CH:2]1.CC(C)=[O:27].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.O>[N:1]1([CH:6]([CH2:17][CH2:18][CH2:19][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][C:15]([OH:27])=[O:16])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 8669165410-(1H-imidazol-1-yl)octadecan-1-olHCID 131709961Jones' reagent

Product 1

HCID 8669165510-(1H-imidazol-1-yl)octadecanoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

10-(1H-imidazol-1-yl)octadecan-1-ol (210 mg, 0.63 mmol) was dissolved in acetone (5 ml) and water (2.5 ml), then Jones reagent (0.75 ml) was added at 0° C. and stirring continued for 3 h at room temperature. The reaction mixture was concentrated and diluted with water (10 ml), and extracted with DCM (3×10 ml), then the combined organic layers were washed with brine solution, dried on MgSO4 and concentrated. The crude compound was purified by silica gel column (3-5% MeOH in DCM) to give 10-(1H-imidazol-1-yl)octadecanoic acid (185 mg, 84%) as a gummy liquid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (10 ml)
  3. extractionextracted with DCM (3×10 ml)
  4. washthe combined organic layers were washed with brine solution
  5. customdried on MgSO4
  6. concentrationconcentrated
  7. customThe crude compound was purified by silica gel column (3-5% MeOH in DCM)

Sources & evidence

ORD record
ord-54d820c91287457b9263d5de6064077f
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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