1-chloro-4-prop-2-enylbenzene

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

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

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

Procedure: To a suspension of magnesium turnings (9.6 g) in anhydrous ether (50 ml) was added dropwise to a solution of p-chlorobromobenzene (76.6 g) in anhydrous ether (500 ml) at such a rate as to maintain reflux. After refluxing for a further 20 minutes, the solution was cooled to 5o and a solution of allyl bromide (48.4 g) in anhydrous ether (100 ml) was added over 15 minutes. After 30 minutes the solution was allowed to warm to room temperature, and then saturated ammonium chloride was added dropwise, cautiously to avoid excessive frothing. The organic layer was separated and the aqueous phase was extracted with ether. After washing the ether extracts with water and drying, evaporation of the solvent gave a pale yellow oil which was purified by fractional distillation to give 3-(4-chlorophenyl)prop-1-ene as a colourless oil, b.p. 72°-74°/4 mm Hg. (532 Pa). to maintain reflux After refluxing for a further 20 minutes The organic layer was separated the aqueous phase was extracted with ether After washing the ether drying evaporation of the solvent gave a pale yellow oil which was purified by fractional distillation