1,3-Dibromopropane → HCID 22326702, compound

HRID 1580046Notes

Reaction equation

HRID 1580046 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[Br:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C.C(Cl)(Cl)Cl>[Br:13][CH2:14][CH2:15][CH2:16][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12]

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 22326702HCID 22326702, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

32.43 g (0.2 mol) 5-hydroxy-1-oxotetraline and 120.14 g (0.6 mol) 1,3-dibromopropane were, while stirring, heated to the boil in 200 ml anhydrous isopropanol and thereafter 41.46 g (0.3 mol) pulverized anhydrous potassium carbonate were added thereto over the course of about three hours. Subsequently, the reaction mixture was vigorously stirred for six hours at reflux temperature, then filtered with suction and the filter cake washed out with isopropanol. The filtrate was evaporated in a vacuum and excess 1,3-dibromopropane was substantially stripped off. The oily evaporation residue obtained was taken up in chloroform, the chloroform solution was extracted several times with a dilute aqueous solution of sodium hydroxide, then shaken with water until neutral and dried. After distilling off the chloroform, the oily residue was distilled at oil pump vacuum. Between 145°-155°C/0.05 mm Hg, there were obtained 32.3 g (57.1% of theory) 5-(3-bromopropoxy)-1-oxotetraline, which was then further worked up.

Workup

  1. additionwere added
  2. customover the course of about three hours
  3. stirringSubsequently, the reaction mixture was vigorously stirred for six hours
  4. temperatureat reflux temperature
  5. filtrationfiltered with suction
  6. washthe filter cake washed out with isopropanol
  7. customThe filtrate was evaporated in a vacuum and excess 1,3-dibromopropane
  8. customThe oily evaporation residue obtained
  9. extractionthe chloroform solution was extracted several times with a dilute aqueous solution of sodium hydroxide
  10. stirringshaken with water until neutral and
  11. customdried
  12. distillationAfter distilling off the chloroform
  13. distillationthe oily residue was distilled at oil pump vacuum

Sources & evidence

ORD record
ord-43b322ee76c64bfc8cde10d53c312f3c
Source dataset
uspto-grants-1976_01
Patent number
US03932411

Reaction notes

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