Sodium Hydroxide → HCID 14327332, compound

HRID 329466Notes

Reaction equation

HRID 329466 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:28]=[CH:27][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[CH:14][CH:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>CO.O>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:28]=[CH:27][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:14][CH:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14327315HCID 14327315, compound

Product 1

HCID 14327332HCID 14327332, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.5 g ethyl 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]hexanoate in 10 ml methanol, was added a solution of 520 mg sodium hydroxide in 5 ml water, and the mixture was heated under reflux for 5 hours. Methanol was distilled off under reduced pressure, and dilute hydrochloric acid was added to the remaining aqueous solution to lower its pH down to about 5. The solid which separated out was collected by filtration, washed with water, and recrystallized from methanol, affording 2 g of 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]hexanoic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. distillationMethanol was distilled off under reduced pressure, and dilute hydrochloric acid
  4. additionwas added to the remaining aqueous solution
  5. customThe solid which separated out
  6. filtrationwas collected by filtration
  7. washwashed with water
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-bc506db50d8543ee818d3f257132edcd
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Reaction notes

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