Propargyl alcohol → 1-Bromo-6-(prop-2-YN-1-yloxy)hexane

HRID 1649788Notes

Reaction equation

HRID 1649788 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][O:4][CH2:1][C:2]#[CH:3]

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 218955011-Bromo-6-(prop-2-YN-1-yloxy)hexaneYield 68.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of propargyl alcohol (5.6 g), 1,6-dibromohexane (73.2 g), tetrabutylammonium bisulphate (0.5 g), and aqueous sodium hydroxide (50%, w/v, 27 ml) was stirred at room temperature for 20 h, diluted with water (50 ml), and extracted with diethyl ether (2×100 ml). The dried extract was evaporated and the residue was purified on a column of silica (Merck 9385) eluting with cyclohexane followed by cyclohexane-diethyl ether (19:1) to give the title compound as a colourless oil (15.0 g), t.l.c. (cyclohexane-diethyl ether 9:1) Rf 0.4.

Workup

  1. extractionextracted with diethyl ether (2×100 ml)
  2. extractionThe dried extract
  3. customwas evaporated
  4. customthe residue was purified on a column of silica (Merck 9385)
  5. washeluting with cyclohexane

Sources & evidence

ORD record
ord-4c22af32127b4a9c902ac0aba2d21e79
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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