Water → 6-Bromohexylbut-3-ynyl ether

HRID 857086Notes

Reaction equation

HRID 857086 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[Br:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.O>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[CH2:1]([O:5][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][Br:6])[CH2:2][C:3]#[CH:4]

Participants

6

Reactant 3

HCID 962WaterHCID 123681,6-DibromohexaneHCID 135663-Butyn-1-OL

Product 1

HCID 113792816-Bromohexylbut-3-ynyl ether

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 14798Sodium HydroxideSolvent

Procedure

3-Butyn-1-ol (42.4 ml) was stirred vigorously with 1,6-dibromohexane (260 ml) and tetrabutylammonium bisulphate (2.4 g) in 50% aqueous sodium hydroxide solution (200 ml) under nitrogen for 3 days. Water (ca 700 ml) was added and the organic layer was separated. The aqueous layer was extracted twice with dichloromethane (2×100 ml) and the combined organic layers were washed with water, dried (MgSO4) and concentrated. The residue in petroleum ether (bp 40–60°) was loaded onto a column of silica gel (1.5 kg) and the column was eluted with petroleum ether (bp 40–60°), then 10% diethyl ether in petroleum ether (bp 40–60°) to give the title compound (103.3 g).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane (2×100 ml)
  3. washthe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washthe column was eluted with petroleum ether (bp 40–60°)

Sources & evidence

ORD record
ord-eb3628cf0a6d4b47937c8935a208efe5
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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