1,5-Dibromopentane → HCID 19798080, compound

HRID 893770Notes

Reaction equation

HRID 893770 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>[OH-].[Na+].S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 81001,5-DibromopentaneHCID 76889Benzenebutanol

Product 1

HCID 19798080HCID 19798080, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 14798Sodium HydroxideSolvent2×

Procedure

4-Phenylbutanol (5.80 g) was stirred in 1,5-dibromopentane (52 ml) and 5N NaOH solution (50 ml), and tetrabutyl ammonium bisulphate (0.87 g) was added and the reaction mixture was stirred at RT for 72 h. (After 42 h the NaOH layer was replaced by a fresh solution). The two layers were separated and the aqueous phase was extracted with ER (3×50 ml). The combined organic layers were dried (Na2SO4), and evaporated to give a clear liquid. Excess 1,5-dibromopentane was removed by distillation at 60° 1.00 mmHg. The residue was chromatographed on a silica (70-230 mesh, 30 g) column using CX as eluant, with a slowly increasing quantity of ER until the title compound was obtained, which on evaporation gave a colorless oil (3.26 g). T.l.c. (CX-ER (99:1)) Rf 0.15.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous phase was extracted with ER (3×50 ml)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customevaporated
  5. customto give a clear liquid
  6. customExcess 1,5-dibromopentane was removed by distillation at 60° 1.00 mmHg
  7. customThe residue was chromatographed on a silica (70-230 mesh, 30 g) column
  8. temperaturewith a slowly increasing quantity of ER until the title compound
  9. customwas obtained
  10. customwhich on evaporation

Sources & evidence

ORD record
ord-b17f4a2d70d041a1b5452b8a13c25fd6
Source dataset
uspto-grants-1992_06
Patent number
US05126375

Reaction notes

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