Sodium Hydroxide → HCID 14327319, compound

HRID 329465Notes

Reaction equation

HRID 329465 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23]CC)=[O:22])[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>C(O)C>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([CH3:26])([CH3:27])[C:21]([OH:23])=[O:22])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14327318HCID 14327318, compound

Product 1

HCID 14327319HCID 14327319, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.5 g ethyl 6-[m-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanoate, 20 ml of 1N NaOH solution and 20 ml ethanol was heated under reflux overnight. Ethanol was distilled off under reduced pressure, and concentrated hydrochloric acid was added to the remaining aqueous solution to lower its pH down to about 4.0. The pasty solid which separated out was extracted with chloroform, and the extract was washed with water and dried. The solvent was distilled off, and the crude product thus obtained was purified by silica gel column chromatography, affording 3.2 g of 6-[m-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanoic acid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. distillationEthanol was distilled off under reduced pressure, and concentrated hydrochloric acid
  4. additionwas added to the remaining aqueous solution
  5. customThe pasty solid which separated out
  6. extractionwas extracted with chloroform
  7. washthe extract was washed with water
  8. customdried
  9. distillationThe solvent was distilled off
  10. customthe crude product thus obtained
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0a3847fdbb9349669f8035224f3dd27c
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Reaction notes

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