1,3-Dibromopropane → 5-(3-Bromopropoxy)-1,2,3,4-tetrahydronaphthalene

HRID 1383147Notes

Reaction equation

HRID 1383147 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]Br>C(Cl)Cl.O.S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br: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 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 144059475-(3-Bromopropoxy)-1,2,3,4-tetrahydronaphthaleneYield 66.5%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure of Example 7 using 5,6,7,8-tetrahydronaphthalene-1-ol (10 g, 0.067 mol) in methylene chloride (100 ml), sodium hydroxide (5.5 g, 0.134 mol) in water (100 ml), 1,3-dibromopropane (47 g, 0.23 mol) and tetra-n-butylammonium bisulfate (23 g, 0.067 mol). Chromatography of the crude product on silica gel using 1% ethyl acetate/hexane as eluent gave 12 g (60%) of the title compound as an oil.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6f6eb6588b93405696c596dd7f11f69e
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

Loading…