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

HRID 1383138Notes

Reaction equation

HRID 1383138 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-].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>C(Cl)Cl.O.S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][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 961HydroxideHCID 80561,4-DibromobutaneHCID 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-tetrahydronaphthalen-1-ol (4.2 g, 0.028 mol) in methylene chloride (50 ml) was mixed with a solution of sodum 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-98adefce115d43558537414de761415b
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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