2-(2-methylphenyl)oxirane

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

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

Procedure: Similarly a mixture of 13.6 g. (0.0753 mol) of 3,4-dimethoxyphenylethylamine and 10.1 g. (0.753 mol) of o-methylstyrene oxide is stirred at 100° C. under argon for 16 hours to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methylphenyl)ethylamine, m.p. 91°-94° C. Similarly a mixture of 13.6 g

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

Procedure: Similarly a mixture of 13.6 g. (0.0753 mol) of 3,4-dimethoxyphenylethylamine and 10.1 g. (0.753 mol) of o-methylstyrene oxide is stirred at 100° C. under argon for 16 hours to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methylphenyl)ethylamine, m.p. 91°-94° C. Similarly a mixture of 13.6 g

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

Procedure: Following the procedure of Example 9 and employing a 57% dispersion sodium hydride in mineral oil (4.84 g., 0.115 mol), 23.5 g. (0.115 mol) of trimethylsulfonium iodide and 11.5 g. (0.0926 mol) of o-tolualdehyde there is obtained o-methylstyrene oxide.

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

Procedure: Similarly a mixture of 13.6 g. (0.0753 mol) of 3,4-dimethoxyphenethylamine and 10.1 g. (0.753 mol) of o-methylstyrene oxide is stirred at 100° C. under argon for 16 hours to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methylphenyl)ethylamine, m.p. 91°-94° C. Similarly a mixture of 13.6 g

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

Procedure: Similarly a mixture of 13.6 g. (0.0753 mol) of 3,4-dimethoxyphenethylamine and 10.1 g. (0.753 mol) of o-methylstyrene oxide is stirred at 100° C. under argon for 16 hours to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methylphenyl)ethylamine, m.p. 91°-94° C. Similarly a mixture of 13.6 g

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

Procedure: Following the procedure of Example 16 and employing 57% sodium hydride (4.84 g., 0.115 mol), 23.5 g. (0.115 mol) of trimethylsulfonium iodide and 11.5 g. (0.0926 mol) of o-tolualdehyde there is obtained o-methylstyrene oxide.

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

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

Procedure: Homoveratrylamine (13.6 g, 0.0753 mole) and o-methylstyrene oxide (10.1 g, 0.0753 mole) were stirred at 100° under argon for 16 hours and then diluted with benzene and hexane and cooled in ice. The solid which precipitated was filtered and recrystallized from benzene-hexane to give 8.6 g (36%) of 2-methyl-α-[N-(3,4-dimethoxyphenethyl)aminomethyl]benzyl alcohol, mp 91°-94°. cooled in ice The solid which precipitated was filtered recrystallized from benzene-hexane

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

Procedure: Sodium hydride (57%) (4.84 g., 0.115 mole) previously washed with hexane was stirred with dry dimethylsulfoxide (70 ml) at 65°-70° for 2 hours under argon. The mixture was diluted with dry THF (70 ml), cooled to -5° and trimethylsulfonium iodide (23.5 g, 0.115 mole) in 100 ml of dry DMSO was added over a period of 3 minutes. After stirring for one minute o-tolualdehyde (11.5 g, 0.0926 mole) was added at a moderate rate while keeping the reaction mixture at 0° to -5°. The mixture was stirred at 0° for 5 minutes and at room temperature for 1 hour, diluted with 500 ml of ice water and extracted three times with ether. The ether solution was washed with saturated sodium chloride, dried with sodium sulfate and evaporated to an oil which was distilled under reduced pressure (~0.25-0.50 mm) to give 10.25 g (83 %) of o-methylstyrene oxide as a clear liquid (b.p. 35°-38°). cooled to -5° was added at a moderate rate at 0° to -5° extracted three times with ether The ether solution was washed with saturated sodium chloride dried with sodium sulfate evaporated to an oil which was distilled under reduced pressure (~0.25-0.50 mm)

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

Procedure: Similarly a mixture of 13.6 g. (0.0753 mol) of 3,4-dimethoxyphenylethylamine and 10.1 g. (0.753 mol) of o-methylstyrene oxide is stirred at 100° C. under argon for 16 hours to yield N-[2-(3,4-dimethoxyphenyl)ethyl]-2-hydroxy-2-(2-methylphenyl)ethylamine, m.p. 91°-94° C. Similarly a mixture of 13.6 g

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

Procedure: Following the procedure of Example 9 and employing a 57% dispersion sodium hydride in mineral oil (4.84 g., 0.115 mol), 23.5 g. (0.115 mol) of trimethylsulfonium iodide and 11.5 g. (0.0926 mol) of o-tolualdehyde there is obtained o-methylstyrene oxide.