Sodium Hydroxide → HCID 22916392, compound

HRID 1616568Notes

Reaction equation

HRID 1616568 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][N:15]=[C:14]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O.CO>[C:18]1([C:14]2[N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:24])=[O:4])[CH:17]=[CH:16][N:15]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59167796HCID 59167796, compound

Product 1

HCID 22916392HCID 22916392, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add sodium hydroxide (6.0 g, 150 mmol) in water (50 mL) to a suspension of 8-(2-phenylimidazol-1-yl)octanoic acid methyl ester (7.60 g, 25 mmol) in methanol (100 mL) at 0° C. under nitrogen. Warm the mixture to room temperature and stir for a total of 8 hours. Remove the solvent under reduced pressure, dilute the residue with water (300 mL), cool to 0° C., and acidify to pH 1 with 1 N HCl. Collect the precipitate and triturate with hexanes to afford 8-(2-phenylimidazol-1-yl)octanoic acid (4.22 g, 52%). APCI mass spectrum m/z 285 [C17H22N2O2—H]−.

Workup

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with water (300 mL)
  3. temperaturecool to 0° C.
  4. customCollect the precipitate
  5. customtriturate with hexanes

Sources & evidence

ORD record
ord-18d9c0ce355f4f599c0c930dc1bd5c28
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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