Reaction of cyclohexene with oxone

Objetives

Epoxidation of an alkene, in this particular cyclohexene, using an easy-to-handle oxidant such as Oxone®.

reaction of cyclohexene with oxone

Background

The typical procedure of alkene epoxidation calls for peracids in an organic solvent. One of the most common experimental methods consists of the reaction of peracetic acid in acetic acid. The peracid is generated in situ by the addition of hydrogen peroxide. The proposed green oxidation of one alkene to give the corresponding epoxide is to use the handle itself and save oxidant Oxone® (2KHSO5 · KHSO4 · K2SO4). Epoxidation takes place in a tandem reaction. Oxone® reacts with acetone and sodium bicarbonate to produce dimethyl-dioxirane, and, in the presence of an alkene such as cyclohexene, it is converted to the corresponding epoxide.

Experimental procedure

In a round-bottom flask equipped with a stir bar, prepare a solution of cyclohexene (10 mmol, 0.82 g) in acetone (30 ml). To this solution, add NaHCO3 (4 g, 47.6 mmol) and cool the mixture solution in an ice bath to 0 ºC. In another flask, add dropwise a solution of Oxone® (8.0 g, 13.0 mmol) in water (30 ml). When the addition is complete, remove the mixture from the ice bath, and allow it to reach r.t. while stirring. After 30 min, the reaction is complete. Transfer the reaction mixture to a separatory funnel, and extract with two aliquots of diethyl ether (2 × 25 ml). Combine the organic layers and place back into the separatory funnel and wash with 20 ml of water. Transfer the organic layer to an Erlenmeyer and then dry over anhydrous MgSO4, gravity filter, and transfer to a round-bottom flask. The solvent is removed in a rotary evaporator to give the crude epoxide in nearly quantitative yield.

Physico-chemical properties

This table collects data for the molecular weight (Mw), melting point (M.p.) boiling point (B.p.) and density of the reactives and compounds used in this laboratory experiment.

Name Mw (g/mol) M.p. (ºC) B.p. (ºC) Density (g/ml)
Oxone®614.78 - - -
Cyclohexene82.14-104830.779
Diethyl ether74.12-11634.60.71
NaHCO384.01300 -2.160
MgSO4120.371124 -1.070

GHS pictograms

Hazard pictograms form part of the international Globally Harmonized System of Classification and Labelling of Chemicals (GHS) and are collected in the followinf Table for the chemical compounds used in this experiment.

Name GHS
Oxone® ghs03  Danger Warning Oxidizing pictogram ghs05  Danger Warning Corrosive cat. 1 pictogram ghs07  Warning Toxic cat. 4 Irritant cat. 2 or 3 Lower systemic health hazards pictogram ghs08  Danger Warning Systemic health hazards pictogram
Cyclohexene ghs02  Danger Warning Flammable pictogram ghs06  Danger Toxic cat. 1–3 pictogram ghs08  Danger Warning Systemic health hazards pictogram
Diethyl ether ghs02  Danger Warning Flammable pictogram ghs07  Warning Toxic cat. 4 Irritant cat. 2 or 3 Lower systemic health hazards pictogram
NaHCO3 Non-hazardous
MgSO4 Non-hazardous

International Chemical Identifier

The IUPAC InChI key identifiers for the main compounds used in this experiment are provided to facilitate the nomenclature and formulation of chemical compounds and the search for information on the Internet for these compounds.

Oxone®HJKYXKSLRZKNSI-UHFFFAOYSA-I
CyclohexeneHGCIXCUEYOPUTN-UHFFFAOYSA-N
Diethyl etherRTZKZFJDLAIYFH-UHFFFAOYSA-N
NaHCO3UIIMBOGNXHQVGW-UHFFFAOYSA-M
MgSO4CSNNHWWHGAXBCP-UHFFFAOYSA-L

References

Return to the Organic Synthesis Experiments.

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