1,3-dichloro-2-methylbenzene

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: 270 g of this catalyst was charged into the same fluidized bed reactor as used in Example 1. The catalyst layer was kept at 390° C. To the catalyst layer were fed air, 2,6-dichlorotoluene containing 2% of ethyl bromide, and ammonia at rates of 71.6 N liters, 25.0 g, and 17 N liters per hour, respectively. The ratio of 2,6-dichlorotoluene:oxygen:ammonia was 1.0:4.2:5.0. 2,6-dichlorobenzonitrile was obtained in an amount of 21.5 g per hour. The quantity of unreacted 2,6-dichlorotoluene was 1.6 g. Conversion was 94.5%, yield was 82.3%, and selectivity was 87.1%. was kept at 390° C

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

Procedure: 300 g of this catalyst was placed in a fluidized bed reactor, 1.5 inches in inside diameter and 100 cm high, and was heated therein at 360° C. To this catalyst layer were fed air, 2,6-dichlorotoluene containing 2% of ethyl bromide, and ammonia at rates of 75.2 N liters, 38.2 g, and 15.7 N liters per hour, respectively. The ratio of 2,6-dichlorotoluene:oxygen:ammonia was 1:3:3. 2,6-dichlorobenzonitrile was obtained in an amount of 34.7 g per hour. The quantity of unreacted 2,6-dichlorotoluene was 0.8 g. Conversion was 97.9%, yield was 86.7%, and selectivity was 88.5%. 1.5 inches in inside diameter and 100 cm high, and was heated at 360° C

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

Procedure: 8.1 g (0.05 mol) of 2,6-dichlorotoluene and 9.9 g (0.15 mol) of potassium hydroxide (85%) are heated in 40 ml of methanol in an autoclave at 160° C. for 20 hours, and the pressure rises to about 12 bar. After cooling, the reaction mixture is poured into about 250 ml of water and extracted three times with about 70 ml of dichloromethane. The united organic phases are dried over sodium sulphate and evaporated under reduced pressure. 3-Chloro-2-methylanisole is obtained as an oil (2.5 g, GC analysis: 37.1%, 12% of theory). After cooling extracted three times with about 70 ml of dichloromethane The united organic phases are dried over sodium sulphate evaporated under reduced pressure

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

Procedure: 8.1 g (0.05 mol) of 2,6-dichlorotoluene and 9.9 g (0.15 mol) of potassium hydroxide (85%) are heated in 40 ml of methanol in an autoclave at 200° C. for 20 hours, which results in a pressure of 30 bar. After cooling, the reaction mixture is poured into 250 ml of water and extracted three times with 70 ml of dichloromethane. The aqueous phase is acidified to pH 1-2 with 30% hydrochloric acid and again extracted three times with 70 ml of dichloromethane each time. The united organic phases are dried over sodium sulphate and evaporated under reduced pressure to give a solid. 3-Chloro-2-methylphenol is obtained as a solid (6.2 g, content by HPLC: 93.5%, 82% of theory). which results in a pressure of 30 bar After cooling extracted three times with 70 ml of dichloromethane again extracted three times with 70 ml of dichloromethane each time The united organic phases are dried over sodium sulphate evaporated under reduced pressure to give a solid

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

Procedure: 16.1 g (0.1 mol) of 2,6-dichlorotoluene, 19.8 g (0.3 mol) of potassium hydroxide (85%) and 0.3 g of dibenzo-18-crown-6 are heated in 30 ml of diethylene glycol at a bath temperature of 190° C. with reflux for 16 hours. The water released during the reaction is distilled off. After cooling, the reaction mixture is stirred with 100 ml of water until a solution is obtained and extracted three times with 50 ml of dichloromethane. The aqueous phase is admixed with 35 ml of 30% hydrochloric acid and extracted three times with 70 ml of dichloromethane. The organic phases are dried and concentrated under reduced pressure. 3-Chloro-2-methylphenol is obtained as a solid (11.5 g, content by HPLC: 97%, 78% of theory). with reflux for 16 hours is distilled off After cooling is obtained extracted three times with 50 ml of dichloromethane extracted three times with 70 ml of dichloromethane The organic phases are dried concentrated under reduced pressure

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

Procedure: 16.1 g (0.1 mol) of 2,6-dichlorotoluene and 19.8 g (0.3 mol) of potassium hydroxide (85%) are heated in 30 ml of diethylene glycol at a bath temperature of 190° C. for 18 hours. The water released by the reaction is distilled off. After cooling, the reaction mixture is stirred with 100 ml of water until a solution is obtained and extracted three times with 50 ml of dichloromethane. The aqueous phase is admixed with 35 ml of 30% hydrochloric acid and extracted three times with 70 ml of dichloromethane. The organic phases are dried over sodium sulphate and concentrated under reduced pressure. 3-Chloro-2-methylphenol is obtained as a solid (12.4 g, content by HPLC: 83%, 72% of theory). is distilled off After cooling is obtained extracted three times with 50 ml of dichloromethane extracted three times with 70 ml of dichloromethane The organic phases are dried over sodium sulphate concentrated under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 200 g (1.24 mol) of 2,6-dichlorotoluene were dissolved in 600 ml of hexamethylphosphoramide and treated with 130.41 g (1.86 mol) of sodium thiomethoxide. The mixture was then heated at 100° C. for 3 h. It was allowed to cool, 88.2 g (0.5 mol) of iodomethane were added and it was stirred at room temperature for 0.5 h. The mixture was then added to 3.5 l of water and extracted with ethyl acetate. The combined organic phases were washed with water, dried over MgSO4 and completely concentrated on a rotary evaporator. to cool extracted with ethyl acetate The combined organic phases were washed with water dried over MgSO4 completely concentrated on a rotary evaporator

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

Procedure: 96 g (4 moles) of Mg turnings in 60 ml of absolute tetrahydrofuran (THF) are initially taken under a nitrogen atmosphere. 1 ml of 1,2-dibromoethane is added at 65° C., after which a solution of 644 g (4 moles) of 2,6-dichlorotoluene in 1.5 1 of absolute THF is added dropwise in the course of 21/4 hours. Thereafter, the mixture is stirred for 4 hours under reflux and cooled to room temperature, and 352.8 g (3.6 moles) of cyclohexanone in 250 ml of absolute THF are added under nitrogen. When the reaction is complete, the Grignard reaction mixture is worked up in an aqueous medium in a conventional manner and the solvent is substantially removed by distillation under reduced pressure. The residue is subjected to incipient distillation (30°-107° C./0.27 mbar). The remaining crude product (676 g), which contains as much as 90% of 1-(3'-chloro-2'-methylphenyl)-cyclohexanol, can be further purified by column chromatography using toluene as the mobile phase. under reflux the Grignard reaction mixture the solvent is substantially removed by distillation under reduced pressure The residue is subjected to incipient distillation (30°-107° C./0.27 mbar) can be further purified by column chromatography