1,5-Dibromopentane → HCID 14349184, compound

HRID 2291302Notes

Reaction equation

HRID 2291302 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[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][C:10]([CH3:15])([CH3:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 13422047HCID 13422047, compound

Product 1

HCID 14349184HCID 14349184, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.52 g of methyl 5-(p-hydroxyphenoxy)-2,2-dimethylpentanoate and 1.38 g of anhydrous potassium carbonate was added 30 ml of ethanol and the mixture was heated under reflux for 30 minutes while stirring. After cooling, 2.53 g of 1,5-dibromopentane was added thereto and the mixture was reacted overnight with heating under reflux. After the solvent was removed by distillation under reduced pressure, water was added to the resulting residue followed by extracting with chloroform. After the chloroform layer was successively washed with an aqueous saturated hydrogen sodium carbonate solution and then an aqueous saturated sodium chloride solution, the chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the resulting residue was subjected to silica gel column chromatography. The product was eluted using an n-hexane-ethyl acetate mixture (8:1 in a volume ratio). The solvent was removed by distillation to give the desired product, methyl 5-[p-(5-bromopentyloxy)phenoxy]-2,2-dimethylpentanoate as an oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. customthe mixture was reacted overnight
  5. temperaturewith heating
  6. temperatureunder reflux
  7. customAfter the solvent was removed by distillation under reduced pressure, water
  8. additionwas added to the resulting residue
  9. extractionby extracting with chloroform
  10. washAfter the chloroform layer was successively washed with an aqueous saturated hydrogen sodium carbonate solution
  11. dry with materialan aqueous saturated sodium chloride solution, the chloroform layer was dried over anhydrous sodium sulfate
  12. customThe solvent was removed by distillation under reduced pressure
  13. washThe product was eluted
  14. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-d5038d0150bc46c188af92c5080853a5
Source dataset
uspto-grants-1989_01
Patent number
US04795753

Reaction notes

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