2-methoxy-1,3-dimethylbenzene

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:

Conditions: temp:80.01; 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:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Succinic anhydride (22.06 gm) was added to a mixture of 2,6-dimethylanisole (30 g) and anhydrous aluminium trichloride (59 g) in 1,2-dichloroethane (200 ml) at 0° C. The mixture was stirred for 0.5 hr at 0° C. and at room temperature for 4 hr. The mixture was poured onto ice-concentrated hydrochloric acid. After stirring vigorously for 5 min, the mixture was extracted with ethyl acetate. The dried (MgSO4) organic fraction was evaporated to give 4-(3,5-dimethyl-4-methoxyphenyl)-4-oxobutyric acid as white crystals, mp 108° C. The mixture was poured onto ice-concentrated hydrochloric acid After stirring vigorously for 5 min the mixture was extracted with ethyl acetate The dried (MgSO4) organic fraction was evaporated

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

Procedure: Bromine is added dropwise to a solution of 2,6-dimethylanisole (12.0 g) in chloroform (100 ml) at about 5°. The solution is stirred at 5° for 2 hr and then allowed to warm to 20°-25°. The reaction mixture is poured into ice-water, and the phases are separated. The chloroform phase is washed with water, aqueous sodium bisulfite solution, then with water, dried over sodium sulfate and concentrated under reduced pressure to give 3,5-dimethyl-4-methoxybromobenzene. to warm to 20°-25° the phases are separated The chloroform phase is washed with water, aqueous sodium bisulfite solution with water, dried over sodium sulfate concentrated under reduced pressure