Butyl bromide → HCID 14555678, compound

HRID 1723415Notes

Reaction equation

HRID 1723415 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[CH:4][CH:3]=1.C(COC)OC.Br[CH2:27][CH2:28][CH2:29][CH3:30]>C(O)C.[OH-].[K+]>[CH2:27]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:6][CH:7]=1)[CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 80711,2-DimethoxyethaneHCID 14555676HCID 14555676, compound

Product 1

HCID 14555678HCID 14555678, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent2×

Procedure

A mixture of 7 gms 9(4-hydroxyphenyl)nonanoic acid, methyl ester, 1.45 gms KOH, 100 ml dry dimethoxyethane, and 3.6 gms 1-bromobutane was refluxed with stirring for 24 hrs. The reaction was cooled, filtered through diatomaceous earth, and the solvent was removed in vacuo. The residue was dissolved in CHCl3, washed twice with 5% Na2CO3, twice with water and once with NaCl solution, and dried over MgSO4. The drying agent was filtered off and the solvent removed in vacuo to give an oil. This oil was stirred overnight at room temperature in a mixture of 70 ml ethanol and 30 ml 10% KOH solution. The solvent was then evaporated in vacuo, the residue dissolved in hot water, cooled, acidified, and the precipitated solid filtered off. The solid was boiled with hexane, filtered, and the solid boiled with cyclohexane and filtered. The insoluble material was again dissolved in water, the aqueous phase acidified with HCl, and the resulting solid was boiled with hexane and filtered. All hexane and cyclohexane solutions were combined and evaporated in vacuo to give 3.5 gms of solid m.p. 45°-8°, which was used directly in the next step.

Workup

  1. temperaturewas refluxed
  2. temperatureThe reaction was cooled
  3. filtrationfiltered through diatomaceous earth
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in CHCl3
  6. washwashed twice with 5% Na2CO3, twice with water and once with NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationThe drying agent was filtered off
  9. customthe solvent removed in vacuo
  10. customto give an oil
  11. customThe solvent was then evaporated in vacuo
  12. dissolutionthe residue dissolved in hot water
  13. temperaturecooled
  14. filtrationthe precipitated solid filtered off
  15. filtrationfiltered
  16. filtrationfiltered
  17. dissolutionThe insoluble material was again dissolved in water
  18. filtrationfiltered
  19. customevaporated in vacuo

Sources & evidence

ORD record
ord-0c785271a08d447a83fd73da07bc851e
Source dataset
uspto-grants-1989_08
Patent number
US04861798

Reaction notes

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