2-hydroxyethyl 2-methylpropanoate

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

Procedure: To a suspension of isobutyric acid (5 g, 0.056 mol) and ethylene glycol (15.8 g, 0.283 mol.) was added dropwise Sulfuric acid (cat. 0.4 mL). The resulting mixture was heated at 80° C. for 4 hrs. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was then cooled down to rt, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 2-hydroxyethyl isobutyrate isolated as a colorless oil. The reaction mixture was then cooled down to rt washed with saturated aqueous sodium bicarbonate solution dried over magnesium sulfate evaporated

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

Procedure: To a suspension of isobutyric acid (5 g, 0.056 mol) and ethylene glycol (15.8 g, 0.283 mol.) was added dropwise Sulfuric acid (cat. 0.4 mL). The resulting mixture was heated at 80° C. for 4 hrs. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was then cooled down to rt, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 2-hydroxyethyl isobutyrate isolated as a colorless oil. The reaction mixture was then cooled down to rt washed with saturated aqueous sodium bicarbonate solution dried over magnesium sulfate evaporated

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

Procedure: 19.5 g (0.0822 mol) of 3,5-dinitrophenyl carbonyl azide was placed, in a nitrogen current, in a 0.3-l four-necked flask equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added acetonitrile for dissolution and the total amount was made 50 ml. The flask contents were heated for refluxing to obtain 50 ml of an acetonitrile solution containing 3,5-dinitrophenyl isocyanate (compound 7). While the flask was being cooled with ice water, 12.0 g (0.0909 mol) of 2-hydroxyethyl 2-methylpropionate was dropwise added to the flask contents with stirring. After the dropwise addition, stirring was conducted at room temperature for 2 hours; 50 ml of water was added; and stirring was conducted for several minutes. Then, dichloromethane was added. All the flask contents were transferred into a separating funnel for separation of the aqueous layer. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from butanol to obtain 2-(3,5-dinitrophenylcarbamoyloxy)ethyl isobutyrate (compound 8) as a yellow powder. Yield: 14.4 g (50%) Melting point: 94-95° C. equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser for dissolution The flask contents were heated for refluxing was dropwise added to the flask contents After the dropwise addition stirring and stirring was conducted for several minutes All the flask contents were transferred into a separating funnel for separation of the aqueous layer Thereto was added a 5% aqueous sodium carbonate solution by mixing dried over anhydrous magnesium sulfate From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated The solid was recrystallized from butanol

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

Procedure: 19.5 g (0.0822 mol) of 3,5-dinitrophenyl carbonyl azide was placed, in a nitrogen current, in a 0.3-l four-necked flask equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added acetonitrile for dissolution and the total amount was made 50 ml. The flask contents were heated for refluxing to obtain 50 ml of an acetonitrile solution containing 3,5-dinitrophenyl isocyanate (compound 7). While the flask was being cooled with ice water, 12.0 g (0.0909 mol) of 2-hydroxyethyl 2-methylpropionate was dropwise added to the flask contents with stirring. After the dropwise addition, stirring was conducted at room temperature for 2 hours; 50 ml of water was added; and stirring was conducted for several minutes. Then, dichloromethane was added. All the flask contents were transferred into a separating funnel for separation of the aqueous layer. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from butanol to obtain 2-(3,5-dinitrophenylcarbamoyloxy)ethyl isobutyrate (compound 8) as a yellow powder. Yield: 14.4 g (50%) Melting point: 94-95° C. equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser for dissolution The flask contents were heated for refluxing was dropwise added to the flask contents After the dropwise addition stirring and stirring was conducted for several minutes All the flask contents were transferred into a separating funnel for separation of the aqueous layer Thereto was added a 5% aqueous sodium carbonate solution by mixing dried over anhydrous magnesium sulfate From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated The solid was recrystallized from butanol

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

Procedure: 19.5 g (0.0822 mol) of 3,5-dinitrophenyl carbonyl azide was placed, in a nitrogen current, in a 0.3-l four-necked flask equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added acetonitrile for dissolution and the total amount was made 50 ml. The flask contents were heated for refluxing to obtain 50 ml of an acetonitrile solution containing 3,5-dinitrophenyl isocyanate (compound 7). While the flask was being cooled with ice water, 12.0 g (0.0909 mol) of 2-hydroxyethyl 2-methylpropionate was dropwise added to the flask contents with stirring. After the dropwise addition, stirring was conducted at room temperature for 2 hours; 50 ml of water was added; and stirring was conducted for several minutes. Then, dichloromethane was added. All the flask contents were transferred into a separating funnel for separation of the aqueous layer. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from butanol to obtain 2-(3,5-dinitrophenylcarbamoyloxy)ethyl isobutyrate (compound 8) as a yellow powder. Yield: 14.4 g (50%) Melting point: 94-95° C. equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser for dissolution The flask contents were heated for refluxing was dropwise added to the flask contents After the dropwise addition stirring and stirring was conducted for several minutes All the flask contents were transferred into a separating funnel for separation of the aqueous layer Thereto was added a 5% aqueous sodium carbonate solution by mixing dried over anhydrous magnesium sulfate From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated The solid was recrystallized from butanol

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

Procedure: 83 g ((0.36 mol) of 3,5-dinitrobenzoyl chloride (compound 2) and 28 g (0.36 mol) of pyridine were placed in a 1-l four-necked flask equipped with a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added 100 ml of dichloromethane for dissolution. The flask was cooled to 10° C. with ice water. Thereto was dropwise added, in 20 minutes with the temperature (10° C.) being maintained, 62 g (0.47 mol) of 2-hydroxyethyl 2-methylpropionate. After the dropwise addition, the flask was immersed in an oil bath of 50° C. and the flask contents were stirred for 1 hour. The flask was cooled to room temperature and 50 ml of water was added, followed by stirring for several minutes. All the flask contents were transferred into a separating funnel and the aqueous layer was separated to remove. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from a mixed solvent consisting of 200 ml of methanol and 100 ml of water to obtain 2-(3,5-dinitrobenzoyloxy)ethyl isobutyrate (compound 3). Yield: 100 g (86%) Melting point: 55-58° C. equipped with a dropping funnel, a reflux condenser for dissolution Thereto was dropwise added, in 20 minutes with the temperature (10° C.) being maintained After the dropwise addition the flask was immersed in an oil bath of 50° C. by stirring for several minutes All the flask contents were transferred into a separating funnel the aqueous layer was separated to remove Thereto was added a 5% aqueous sodium carbonate solution by mixing dried over anhydrous magnesium sulfate From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated The solid was recrystallized from a mixed solvent

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

Procedure: 83 g ((0.36 mol) of 3,5-dinitrobenzoyl chloride (compound 2) and 28 g (0.36 mol) of pyridine were placed in a 1-l four-necked flask equipped with a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added 100 ml of dichloromethane for dissolution. The flask was cooled to 10° C. with ice water. Thereto was dropwise added, in 20 minutes with the temperature (10° C.) being maintained, 62 g (0.47 mol) of 2-hydroxyethyl 2-methylpropionate. After the dropwise addition, the flask was immersed in an oil bath of 50° C. and the flask contents were stirred for 1 hour. The flask was cooled to room temperature and 50 ml of water was added, followed by stirring for several minutes. All the flask contents were transferred into a separating funnel and the aqueous layer was separated to remove. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from a mixed solvent consisting of 200 ml of methanol and 100 ml of water to obtain 2-(3,5-dinitrobenzoyloxy)ethyl isobutyrate (compound 3). Yield: 100 g (86%) Melting point: 55-58° C. equipped with a dropping funnel, a reflux condenser for dissolution Thereto was dropwise added, in 20 minutes with the temperature (10° C.) being maintained After the dropwise addition the flask was immersed in an oil bath of 50° C. by stirring for several minutes All the flask contents were transferred into a separating funnel the aqueous layer was separated to remove Thereto was added a 5% aqueous sodium carbonate solution by mixing dried over anhydrous magnesium sulfate From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated The solid was recrystallized from a mixed solvent

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

Procedure: To a suspension of isobutyric acid (5 g, 0.056 mol) and ethylene glycol (15.8 g, 0.283 mol.) was added dropwise Sulfuric acid (cat. 0.4 mL). The resulting mixture was heated at 80° C. for 4 hrs. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was then cooled down to rt, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 2-hydroxyethyl isobutyrate isolated as a colorless oil. The reaction mixture was then cooled down to rt washed with saturated aqueous sodium bicarbonate solution dried over magnesium sulfate evaporated

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

Procedure: 19.5 g (0.0822 mol) of 3,5-dinitrophenyl carbonyl azide was placed, in a nitrogen current, in a 0.3-l four-necked flask equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added acetonitrile for dissolution and the total amount was made 50 ml. The flask contents were heated for refluxing to obtain 50 ml of an acetonitrile solution containing 3,5-dinitrophenyl isocyanate (compound 7). While the flask was being cooled with ice water, 12.0 g (0.0909 mol) of 2-hydroxyethyl 2-methylpropionate was dropwise added to the flask contents with stirring. After the dropwise addition, stirring was conducted at room temperature for 2 hours; 50 ml of water was added; and stirring was conducted for several minutes. Then, dichloromethane was added. All the flask contents were transferred into a separating funnel for separation of the aqueous layer. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from butanol to obtain 2-(3,5-dinitrophenylcarbamoyloxy)ethyl isobutyrate (compound 8) as a yellow powder. Yield: 14.4 g (50%) Melting point: 94-95° C. equipped with a nitrogen inlet tube, a dropping funnel, a reflux condenser for dissolution The flask contents were heated for refluxing was dropwise added to the flask contents After the dropwise addition stirring and stirring was conducted for several minutes All the flask contents were transferred into a separating funnel for separation of the aqueous layer Thereto was added a 5% aqueous sodium carbonate solution by mixing dried over anhydrous magnesium sulfate From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated The solid was recrystallized from butanol

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

Procedure: 83 g ((0.36 mol) of 3,5-dinitrobenzoyl chloride (compound 2) and 28 g (0.36 mol) of pyridine were placed in a 1-l four-necked flask equipped with a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added 100 ml of dichloromethane for dissolution. The flask was cooled to 10° C. with ice water. Thereto was dropwise added, in 20 minutes with the temperature (10° C.) being maintained, 62 g (0.47 mol) of 2-hydroxyethyl 2-methylpropionate. After the dropwise addition, the flask was immersed in an oil bath of 50° C. and the flask contents were stirred for 1 hour. The flask was cooled to room temperature and 50 ml of water was added, followed by stirring for several minutes. All the flask contents were transferred into a separating funnel and the aqueous layer was separated to remove. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from a mixed solvent consisting of 200 ml of methanol and 100 ml of water to obtain 2-(3,5-dinitrobenzoyloxy)ethyl isobutyrate (compound 3). Yield: 100 g (86%) Melting point: 55-58° C. equipped with a dropping funnel, a reflux condenser for dissolution Thereto was dropwise added, in 20 minutes with the temperature (10° C.) being maintained After the dropwise addition the flask was immersed in an oil bath of 50° C. by stirring for several minutes All the flask contents were transferred into a separating funnel the aqueous layer was separated to remove Thereto was added a 5% aqueous sodium carbonate solution by mixing dried over anhydrous magnesium sulfate From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated The solid was recrystallized from a mixed solvent

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

Procedure: To a suspension of isobutyric acid (5 g, 0.056 mol) and ethylene glycol (15.8 g, 0.283 mol.) was added dropwise Sulfuric acid (cat. 0.4 mL). The resulting mixture was heated at 80° C. for 4 hrs. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was then cooled down to rt, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 2-hydroxyethyl isobutyrate isolated as a colorless oil. The reaction mixture was then cooled down to rt washed with saturated aqueous sodium bicarbonate solution dried over magnesium sulfate evaporated

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

Procedure: To a suspension of isobutyric acid (5 g, 0.056 mol) and ethylene glycol (15.8 g, 0.283 mol.) was added dropwise Sulfuric acid (cat. 0.4 mL). The resulting mixture was heated at 80° C. for 4 hrs. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was then cooled down to rt, diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 2-hydroxyethyl isobutyrate isolated as a colorless oil. The reaction mixture was then cooled down to rt washed with saturated aqueous sodium bicarbonate solution dried over magnesium sulfate evaporated