1,5-Dibromopentane → HCID 14405946, compound

HRID 1650239Notes

Reaction equation

HRID 1650239 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][CH2:19]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][CH2:19][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 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 14405946HCID 14405946, compoundYield 74.8%

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 tetrahydro naphthalene-1-ol (8 g, 0.054 mol) in methylene chloride (100 ml), sodium hydroxide (4.32 g, 0.108 mol) in water (100 ml), 1,5-dibromopentane (37 g, 0.19 mol) and tetra n-butylammonium bisulfate (18.3 g, 0.054 mol). Chromatography of the crude product on silica gel using 20% ethyl acetate/hexane as eluent gave 12 g (69%) of the title compound as an oil.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f4ed8cc23d07435ab54df2499246e360
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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