1,4-Dibromobutane → 5-(4-Bromobutoxy)-1,2,3,4-tetrahydronaphthalene

HRID 1650235Notes

Reaction equation

HRID 1650235 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>C(Cl)Cl.O.S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][O:11][C:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

7

Reactant 3

HCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 144059455-(4-Bromobutoxy)-1,2,3,4-tetrahydronaphthaleneYield 102.1%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5,6,7,8 tetrahydronaphthalene-1-ol (4.2 g, 0.028 mol) in methylene chloride (50 ml) was mixed with a solution of sodium hydroxide (2.3 g, 0.0575 mol) in water (50 ml). After adding tetra-n butylammonium bisulfate (9.6 g, 0.028 mol) and 1,4-dibromobutane (31 g, 0.14 mol), the reaction mixture was refluxed with vigorous stirring for 2 hrs. The reaction was cooled to room temperature, the layers separated and the organic phase washed with saturated sodium chloride solution. After drying over sodium sulfate, the organic phase was concentrated on the rotary evaporator and the residual oil heated under vacuum (0.1 mm Hg) to remove remaining 1,4-dibromobutane. The residue was chromatographed on silica gel using 100% hexane as eluent to give 8.1 g (71%) of the title compound as an oil.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. customthe layers separated
  3. washthe organic phase washed with saturated sodium chloride solution
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe organic phase was concentrated on the rotary evaporator
  6. temperaturethe residual oil heated under vacuum (0.1 mm Hg)
  7. customto remove
  8. customThe residue was chromatographed on silica gel using 100% hexane as eluent

Sources & evidence

ORD record
ord-ee9f81b569284cba8416cf1ee581f2f6
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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