Sodium Hydroxide → HCID 86691651, compound

HRID 2204035Notes

Reaction equation

HRID 2204035 reaction equation
[N:1]1([CH:6]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18](C(OCC)=O)[C:19]([O:21]CC)=[O:20])[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>CO.O>[N:1]1([CH:6]([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86691650HCID 86691650, compound

Product 1

HCID 86691651HCID 86691651, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl 2-(12-(1H-imidazol-1-yl)hexadecyl)malonate (415 mg, 0.9209 mmol) was dissolved in a 3:1 mixture of methanol (9 ml) and water (3 ml), cooled to 0° C. then NaOH (147 mg, 3.684 mmol) was added and the reaction mixture stirred at room temperature for 3 h. The reaction mixture was then concentrated under reduced pressure to remove MeOH, cooled to 0° C. to 5° C., the pH adjusted to 5, extracted with DCM (3×25 ml), dried on dry MgSO4, and concentrated under reduced pressure. The crude compound was obtained as a light yellow color liquid. This crude compound was heated at 170° C. to remove one carboxyl acid group from the di-carboxylic acid by the evolution of CO2. The crude product was then purified by silica gel column (3 to 5% of MeOH in DCM) to give 14-(1H-imidazol-1-yl)octadecanoic acid (221 mg, 68%) as a pale yellow gummy liquid.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto remove MeOH
  3. temperaturecooled to 0° C. to 5° C.
  4. extractionextracted with DCM (3×25 ml)
  5. dry with materialdried on dry MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude compound was obtained as a light yellow color liquid
  8. customto remove one carboxyl acid group from the di-carboxylic acid by the evolution of CO2
  9. customThe crude product was then purified by silica gel column (3 to 5% of MeOH in DCM)

Sources & evidence

ORD record
ord-dc942e9e85944834b8b8fd65514af5ea
Source dataset
uspto-grants-2016_06
Patent number
US09365597B2

Reaction notes

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