2,3-dimethylbenzaldehyde

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: A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer was charged with 480 parts of 50% formalin, 110 parts of phenol, 202 parts of 98% industrial sulfuric acid, and 424 parts of m-xylene. The resulting mixture was allowed to react at 84° C. to 88° C. for 4 hours. After the reaction was completed, the reaction mixture was allowed to stand to separate a resin phase and a sulfuric acid aqueous phase. The resin phase was washed with water 3 times, and then unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120° C. to 130° C. for 20 minutes. As a result, 480 parts of a phenol-modified xylene-formaldehyde resin having a viscosity of 1,050 mPa·s (25° C.) were obtained. A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer to react at 84° C. to 88° C. for 4 hours to separate a resin phase The resin phase was washed with water 3 times unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120° C. to 130° C. for 20 minutes a viscosity of 1,050 mPa·s (25° C.) were obtained

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

Procedure: A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer was charged with 480 parts of 50% formalin, 110 parts of phenol, 202 parts of 98% industrial sulfuric acid, and 424 parts of m-xylene. The resulting mixture was allowed to react at 84° C. to 88° C. for 4 hours. After the reaction was completed, the reaction mixture was allowed to stand to separate a resin phase and a sulfuric acid aqueous phase. The resin phase was washed with water 3 times, and then unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120° C. to 130° C. for 20 minutes. As a result, 480 parts of a phenol-modified xylene-formaldehyde resin having a viscosity of 1,050 mPa·s (25° C.) were obtained. A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer to react at 84° C. to 88° C. for 4 hours to separate a resin phase The resin phase was washed with water 3 times unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120° C. to 130° C. for 20 minutes a viscosity of 1,050 mPa·s (25° C.) were obtained

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

Procedure: 1B was synthesized from 2,3-dimethylbenzaldehyde (5.0 g, 37.3 mmol) using the procedure described for 1A. Yield: 6.0 g (92%) as light yellow oil. ESI-MS:m/z 176.3 (M+H)+, HPLC retention time: T=1.340 min (FAST-2). T=1.340 min (FAST-2)

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

Procedure: A 2-liter flask equipped with a thermometer, a reflux condenser, and a stirrer was charged with 480 parts of 50% formalin, 110 parts of phenol, 202 parts of 98% industrial sulfuric acid, and 424 parts of m-xylene. The resulting mixture was allowed to react at 84 to 88° C. for 4 hours. A 2-liter flask equipped with a thermometer, a reflux condenser, and a stirrer to react at 84 to 88° C. for 4 hours

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

Procedure: A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer was charged with 480 parts of 50% formalin, 110 parts of phenol, 202 parts of 98% industrial sulfuric acid, and 424 parts of m-xylene. The resulting mixture was allowed to react at 84 to 88° C. for 4 hours. After completion of the reaction, the reaction mixture was allowed to stand to separate a resin phase and a sulfuric acid aqueous phase. After the resin phase was washed with water 3 times, unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120 to 130° C. for 20 minutes. As a result, 480 parts of a phenol-modified xylene-formaldehyde resin having a viscosity of 1,050 mPa·s (25° C.) was obtained. A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer to react at 84 to 88° C. for 4 hours After completion of the reaction to separate a resin phase After the resin phase was washed with water 3 times, unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120 to 130° C. for 20 minutes a viscosity of 1,050 mPa·s (25° C.) was obtained

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

Procedure: A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer was charged with 480 parts of 50% formalin, 110 parts of phenol, 202 parts of 98% industrial sulfuric acid, and 424 parts of m-xylene. The resulting mixture was allowed to react at 84 to 88° C. for 4 hours. After completion of the reaction, the reaction mixture was allowed to stand to separate a resin phase and a sulfuric acid aqueous phase. After the resin phase was washed with water 3 times, unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120 to 130° C. for 20 minutes. As a result, 480 parts of a phenol-modified xylene-formaldehyde resin having a viscosity of 1,050 mPa·s (25° C.) was obtained. A 2-liter separable flask equipped with a thermometer, a reflux condenser, and a stirrer to react at 84 to 88° C. for 4 hours After completion of the reaction to separate a resin phase After the resin phase was washed with water 3 times, unreacted m-xylene was removed under the conditions of 20 to 30 mmHg and 120 to 130° C. for 20 minutes a viscosity of 1,050 mPa·s (25° C.) was obtained

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-(diethoxymethyl)-1H-imidazole (698 mg, 4.10 mmol) in anhydrous tetrahydrofuran (7 ml), at −78° C., was added n-butyllithium (2.5 M in hexane, 1.64 ml, 4.1 mmol). The reaction mixture was stirred at −78° C. for 1 h, before addition of a solution of 2,3-dimethylbenzaldehyde (500 mg, 3.73 mmol) in tetrahydrofuran (3 ml). The reaction mixture was stirred at −78° C. for 2 h, warmed to room temperature and quenched with ice cold hydrochloric acid (4M, 20 ml). The reaction mixture was concentrated in vacuo and to the residue was added water (20 ml). The solution was extracted with diethyl ether (2×20 ml) and the aqueous layer was basified by addition of solid sodium hydrogen carbonate. This solution was extracted with ethyl acetate (3×20 ml) and the combined organic phases were dried (MgSO4) and concentrated in vacuo to give the title compound (543 mg) warmed to room temperature quenched with ice cold hydrochloric acid (4M, 20 ml) The reaction mixture was concentrated in vacuo and to the residue was added water (20 ml) The solution was extracted with diethyl ether (2×20 ml) the aqueous layer was basified by addition of solid sodium hydrogen carbonate This solution was extracted with ethyl acetate (3×20 ml) the combined organic phases were dried (MgSO4) concentrated in vacuo

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,3-dimethylbenzaldehyde (1.0 g, 7.5 mmol) in anhydrous tetrahydrofuran (50 ml), at −78° C. and under nitrogen, was added ethyllithium (0.5M in benzene:cyclohexane 9:1, 14.9 ml, 7.5 mmol), dropwise via syringe. The reaction mixture was stirred at −78° C. for 30 min and then poured into ice cold hydrochloric acid (2N, 20 ml). The mixture was extracted with ethyl acetate (2×50 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (1.22 g). The mixture was extracted with ethyl acetate (2×50 ml) the combined extracts were dried (MgSO4) concentrated in vacuo