Propargyl bromide → 6-[(Prop-2-yn-1-yl)oxy]hexan-1-ol

HRID 1576991Notes

Reaction equation

HRID 1576991 reaction equation
[CH2:1]([OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[H-].[Na+].[CH2:11](Br)[C:12]#[CH:13]>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[CH2:13]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:8])[C:12]#[CH:11]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 123741,6-HexanediolHCID 24758Sodium hydride

Product 1

HCID 200714346-[(Prop-2-yn-1-yl)oxy]hexan-1-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

118 g. of 1,6-hexanediol are introduced into 800 ml. of absolute tetrahydrofuran and, while stirring well, treated portionwise over a period of 4 hours with 30 g. of sodium hydride. 60 ml. of hexamethylphosphoric acid triamide are then added, the mixture is heated to reflux and treated over a period of 12 hours with a solution of 149 g. of propargyl bromide and 200 ml. of tetrahydrofuran. The cooled mixture is poured on to ice-water and extracted three times with ether. The ether solutions are washed with water and sodium chloride solution, dried over sodium sulphate and evaporated. By distillation or chromatography there is obtained pure 6-(2-propynyloxy)-1-hexanol; boiling point (bulb-tube) = 75°C/0.015 mmHg; nD25 = 1.4560.

Workup

  1. additiontreated portionwise over a period of 4 hours with 30 g
  2. temperaturethe mixture is heated
  3. temperatureto reflux
  4. additiontreated over a period of 12 hours with a solution of 149 g
  5. extractionextracted three times with ether
  6. washThe ether solutions are washed with water and sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. distillationBy distillation or chromatography

Sources & evidence

ORD record
ord-66e8a40e0ab84d188d9a2bcebd5fe4d8
Source dataset
uspto-grants-1976_09
Patent number
US03983247

Reaction notes

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