Sodium Hydroxide → YM 212

HRID 329464Notes

Reaction equation

HRID 329464 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:30]=[CH:29][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:28])([CH3:27])[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:30]=[CH:29][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:27])([CH3:28])[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 130328YM 534

Product 1

HCID 129980YM 212Yield 82.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3 g ethyl 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanoate in 15 ml methanol, was added a solution of 580 mg sodium hydroxide in 6 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 2.3 g of 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanoic 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-1cb50b467fbf4a0487eb53b1515f5f66
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Reaction notes

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