3-chloro-2-methylphenol

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: 2 g (9.28 mmol) of epoxide 2h in solution in 5 cm3 of anhydrous DMF were heated to reflux for 3 h. The solution was acidified (pH=1) with 3N HCl, extracted with ether (4×25 cm3), dried over MgSO4, filtered and evaporated down. The crude product obtained was purified by flash chromatography on silica (eluent: ether/petroleum ether=5/95). 1.18 g of phenol 4e were obtained (macrobore GC purity>96%). The yield of compound 4e was 89%. to reflux for 3 h extracted with ether (4×25 cm3) dried over MgSO4 filtered evaporated down The crude product obtained was purified by flash chromatography on silica (eluent: ether/petroleum ether=5/95)

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

Procedure: 3.1 g (0.02 mol) of 3-chloro-2-methylanisole are heated in 20 ml of 50% sulphuric acid for 18 hours with reflux. After cooling, the reaction mixture is extracted three times with dichloromethane, dried over sodium sulphate and concentrated to dryness under reduced pressure. 3-Chloro-2-methylphenol is obtained as a solid (2.9 g, content by HPLC: 11.7%, 12% of theory). with reflux After cooling the reaction mixture is extracted three times with dichloromethane dried over sodium sulphate concentrated to dryness 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:0.00; pressure:0.00; stir:

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of concentrated sulphuric acid (7.3 mL) in water (97 mL) was added to 3-chloro-2-methylaniline (0.84 mL, 7.06 mmol) and the mixture heated at 90° C. until solution was achieved. The reaction mixture was cooled to 0° C. and a solution of sodium nitrite (510 mg, 12.75 mmol) in water (5 mL) was added dropwise. The reaction mixture was allowed to warm to ambient temperature over 2 h. Excess sodium nitrite was destroyed by the addition of urea. The resultant mixture was added to a solution of concentrated sulphuric acid (5.0 mL) in water (55 mL), heated to 90° C. and stirred at this temperature for a further 1 h. The resultant product mixture was filtered through dicalite and extracted with dichloromethane (2×200 mL). The organic phase was washed with NaHCO3 (aq.), dried (MgSO4) and evaporated under reduced pressure to afford the desired product (830 mg, 83%) as an off-white solid. The reaction mixture was cooled to 0° C. to warm to ambient temperature over 2 h Excess sodium nitrite was destroyed by the addition of urea The resultant mixture was added to a solution of concentrated sulphuric acid (5.0 mL) in water (55 mL) heated to 90° C. The resultant product mixture was filtered through dicalite extracted with dichloromethane (2×200 mL) The organic phase was washed with NaHCO3 (aq.) dried (MgSO4) evaporated under reduced pressure