Sodium Hydroxide → 8-[4-(2-Hydroxyphenyl)imidazol-1-yl]octanoic acid

HRID 1616563Notes

Reaction equation

HRID 1616563 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:25])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])[N:15]=[CH:14]1>O.CO>[OH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16]1[N:15]=[CH:14][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:25])=[O:4])[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 684892758-[4-(2-Hydroxyphenyl)imidazol-1-yl]octanoic acid methyl ester

Product 1

HCID 684946238-[4-(2-Hydroxyphenyl)imidazol-1-yl]octanoic acidYield 70.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Add sodium hydroxide (1.32 g, 33 mmol) in water (20 mL) to a suspension of 8-[4-(2-hydroxyphenyl)imidazol-1-yl]octanoic acid methyl ester (2.60 g, 8 mmol) in methanol (50 mL) at 0° C. under nitrogen and warm the mixture to room temperature and stir for 8 hours. Remove the solvent under reduced pressure, dilute the residue with water (200 mL), cool to 0° C., and acidify to pH 1 with 1 N HCl. Collect the precipitate to provide 8-[4-(2-hydroxyphenyl)imidazol-1-yl]octanoic acid (1.70 g, 68%). APCI mass spectrum m/z 301 [C17H22N2O3—H]−.

Workup

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with water (200 mL)
  3. temperaturecool to 0° C.
  4. customCollect the precipitate

Sources & evidence

ORD record
ord-9d345e876606412a93a6fc4f83990bc2
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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