2-[(4-chlorophenyl)methyl]oxirane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of potassium carbonate (8.14 g) and 1,2,4-triazole (8.14 g) in acetonitrile (100 ml) was added 1-(4-chlorophenyl)-2,3-epoxypropane (9.0 g), and the resulting suspension was heated to 70° for 4.5 h. The excess acetonitrile was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and dried, and the solvent was evaporated to give a colourless oil. Purification by column chromatography on silica, eluting with chloroform/methanol, 95:5 by volume, gave 1-(4-chlorophenyl)-3-(1,2,4-triazol-1-yl)-2-propanol as a colourless oil which crystallised on standing, m.p. 104°-6°. the resulting suspension was heated to 70° for 4.5 h The excess acetonitrile was evaporated under reduced pressure the residue was partitioned between ethyl acetate and water The organic layer was separated washed with water dried the solvent was evaporated to give a colourless oil Purification by column chromatography on silica eluting with chloroform/methanol, 95:5 by volume

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-(4-chlorophenyl)prop-1-ene (9.0 g) in chloroform (100 ml) was added portionwise metachloroperbenzoic acid (12.2 g), and the solution was stirred for 5 h at room temperature. The mixture was poured into water, the water layer was separated and the organic layer washed successively with sodium bicaronate, sodium sulphite and water. After drying, evaporation of the solvent gave 1-(4-chlorophenyl)-2,3-epoxypropane as a pale yellow oil. (9.51 g). NMR in CDCl3 : the water layer was separated the organic layer washed successively with sodium bicaronate, sodium sulphite and water After drying evaporation of the solvent