1,5-Dibromopentane → HCID 14327270, compound

HRID 329456Notes

Reaction equation

HRID 329456 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:16])([CH3:15])[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br>C(O)C>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH3:15])([CH3:16])[C:12]([NH2:14])=[O:13])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 14835901HCID 14835901, compound

Product 1

HCID 14327270HCID 14327270, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.0 g 6-(4-hydroxyphenoxy)-2,2-dimethylhexanamide, 50 ml ethanol, 2.5 g potassium carbonate and 3.6 g 1,5-dibromopentane was heated under reflux overnight with stirring. The solvent was distilled off under reduced pressure, the residue was extracted with chloroform, the extract was washed with water and worked up as usual. The crude product thus obtained was purified by silica gel column chromatography, affording 2.90 g of 6-[p-(5-bromopentyloxy)phenoxy]-2,2-dimethylhexanamide.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washthe extract was washed with water
  6. customThe crude product thus obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-047cc12e9fa148b3be26084dc98531fc
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Reaction notes

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