1-Tetradecene → 1,2-Epoxytetradecane

HRID 1165246

Reaction equation

HRID 1165246 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].ClC1C=CC=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH2:3]([CH:2]1[CH2:1][O:23]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 142601-TetradeceneHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 186041,2-Epoxytetradecane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a flask equipped with a mechanical stirrer and an addition funnel was placed 19.8 g (0.1 mole) of 1-tetradecene and 150 ml of CH2Cl2. The solution was stirred and a suspension of 23 g(0.106 mole) of m-chloroperbenzoic acid in 250 ml of CH2Cl2 was added dropwise. After stirring overnight, the CH2Cl2 solution was washed with 10% aqueous NaHSO3, saturated NaHCO3 solution and then dried over Na2SO4. The residue, after removal of solvent, was distilled through a vigreux column to obtain the title compound, bp 78°-81°/0.01 mmHg as a colorless liquid.

Workup

  1. customIn a flask equipped with a mechanical stirrer and an addition funnel
  2. additionwas added dropwise
  3. stirringAfter stirring overnight
  4. washthe CH2Cl2 solution was washed with 10% aqueous NaHSO3, saturated NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. customThe residue, after removal of solvent
  7. distillationwas distilled through a vigreux column

Sources & evidence

ORD record
ord-7f5ddca9f8cd4d2aaec89677a2a551dc
Source dataset
uspto-grants-1990_03
Patent number
US04908384

Linked notes

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