diethyl 2,2-bis(2-cyanoethyl)propanedioate

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

Procedure: To a solution of diethyl malonate (81 g) in 100 g of 1,4-dioxane containing Triton B (10g of 40% methanol solution) was added dropwise acrylonitrile (55 g) in a period of 30 minutes. The reaction is highly exothermic, and the temperature was controlled at 30°-40° C. by means of a water bath. The reaction mixture was stirred overnight, and later poured into 600 ml of ice-water containing hydrochloric acid (5 ml of conc. HCl). The white precipitate formed was collected by filtration and washed with water. The crude product (m.p. 61°-63° C., 100% yield) was used for the next step without further purification. the temperature was controlled at 30°-40° C. by means of a water bath The white precipitate formed was collected by filtration washed with water

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

Procedure: Diethyl 2,2-bis(2-cyanoethyl)malonate (2 g, 7.51 mmol) was added to TMAH (25% in water, 10.95 g, 30.04 mmol) at room temperature. The mixture was stirred for 24 hours, and was then cooled to 0° C. A mixture of 12M HCl (2.69 cm3, 32.1 mmol) and ice (3 g) was added and the mixture was extracted with CH2Cl2 (5×50 cm3). The extracts were evaporated under vacuum to give 2,2-bis(2-cyanoethyl)malonic acid (0.25 g, 15.8%) as a colorless very viscous oil (lit decomposed. 158° C.). was added the mixture was extracted with CH2Cl2 (5×50 cm3) The extracts were evaporated under vacuum

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

Procedure: Diethyl 2,2-bis(2-cyanoethyl)malonate (2 g, 7.51 mmol) was added to TMAH (25% in water, 10.95 g, 30.04 mmol) at room temperature. The mixture was stirred for 24 hours, and was then cooled to 0° C. A mixture of 12M HCl (2.69 cm3, 32.1 mmol) and ice (3 g) was added and the mixture was extracted with CH2Cl2 (5×50 cm3). The extracts were evaporated under vacuum to give 2,2-bis(2-cyanoethyl)malonic acid (0.25 g, 15.8%) as a colorless very viscous oil (lit decomposed. 158° C.). was added the mixture was extracted with CH2Cl2 (5×50 cm3) The extracts were evaporated under vacuum

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diethyl malonate (1 g, 6.2 mmol) and Triton B (40% in MeOH, 0.13 g, 0.31 mmol) in dioxane (1.2 cm3) was added dropwise acrylonitrile (0.658 g, 12.4 mmol) and the mixture was stirred at 60° C. overnight. The mixture was then cooled to room temperature and neutralized with 0.1 M HCl (3 cm3) and poured to ice-water (10 cm3). Crystals precipitated during 30 min. These were collected by filtration and recrystallised from EtOH (cooling in freezer before filtering off) to give diethyl 2,2-bis(2-cyanoethyl)malonate (1.25 g, 75.8%) as a white solid, mp 62.2-63.5° C. Crystals precipitated during 30 min These were collected by filtration recrystallised from EtOH (cooling in freezer before filtering off)

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

Procedure: Diethyl 2,2-bis(2-cyanoethyl)malonate (2 g, 7.51 mmol) was added to TMAH (25% in water, 10.95 g, 30.04 mmol) at room temperature. The mixture was stirred for 24 hours, and was then cooled to 0° C. A mixture of 12M HCl (2.69 cm3, 32.1 mmol) and ice (3 g) was added and the mixture was extracted with CH2Cl2 (5×50 cm3). The extracts were evaporated under vacuum to give 2,2-bis(2-cyanoethyl)malonic acid (0.25 g, 15.8%) as a colourless very viscous oil (lit decomposed. 158° C.). was added the mixture was extracted with CH2Cl2 (5×50 cm3) The extracts were evaporated under vacuum

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diethyl malonate (1 g, 6.2 mmol) and Triton B (40% in MeOH, 0.13 g, 0.31 mmol) in dioxane (1.2 cm3) was added dropwise acrylonitrile (0.658 g, 12.4 mmol) and the mixture was stirred at 60° C. overnight. The mixture was then cooled to room temperature and neutralized with 0.1M HCl (3 cm3) and poured to ice-water (10 cm3). Crystals precipitated during 30 min. These were collected by filtration and recrystallised from EtOH (cooling in freezer before filtering off) to give diethyl 2,2-bis(2-cyanoethyl)malonate (1.25 g, 75.8%) as a white solid, mp 62.2-63.5° C. Crystals precipitated during 30 min These were collected by filtration recrystallised from EtOH (cooling in freezer before filtering off)

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

Procedure: Diethyl 2,2-bis(2-cyanoethyl)malonate (2 g, 7.51 mmol) was added to TMAH (25% in water, 10.95 g, 30.04 mmol) at room temperature. The mixture was stirred for 24 hours, and was then cooled to 0° C. A mixture of 12M HCl (2.69 cm3, 32.1 mmol) and ice (3 g) was added and the mixture was extracted with CH2Cl2 (5×50 cm3). The extracts were evaporated under vacuum to give 2,2-bis(2-cyanoethyl)malonic acid (0.25 g, 15.8%) as a colourless very viscous oil (lit decomposed. 158° C.). was added the mixture was extracted with CH2Cl2 (5×50 cm3) The extracts were evaporated under vacuum

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diethyl malonate (1 g, 6.2 mmol) and Triton B (40% in MeOH, 0.13 g, 0.31 mmol) in dioxane (1.2 cm3) was added dropwise acrylonitrile (0.658 g, 12.4 mmol) and the mixture was stirred at 60° C. overnight. The mixture was then cooled to room temperature and neutralized with 0.1 M HCl (3 cm3) and poured to ice-water (10 cm3). Crystals precipitated during 30 min. These were collected by filtration and recrystallised from EtOH (cooling in freezer before filtering off) to give diethyl 2,2-bis(2-cyanoethyl)malonate (1.25 g, 75.8%) as a white solid, mp 62.2-63.5° C. Crystals precipitated during 30 min These were collected by filtration recrystallised from EtOH (cooling in freezer before filtering off)

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

Procedure: To a solution of diethyl malonate (81 g) in 100 g of 1,4-dioxane containing Triton B (10g of 40% methanol solution) was added dropwise acrylonitrile (55 g) in a period of 30 minutes. The reaction is highly exothermic, and the temperature was controlled at 30°-40° C. by means of a water bath. The reaction mixture was stirred overnight, and later poured into 600 ml of ice-water containing hydrochloric acid (5 ml of conc. HCl). The white precipitate formed was collected by filtration and washed with water. The crude product (m.p. 61°-63° C., 100% yield) was used for the next step without further purification. the temperature was controlled at 30°-40° C. by means of a water bath The white precipitate formed was collected by filtration washed with water

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

Procedure: Diethyl 2,2-bis(2-cyanoethyl)malonate (2 g, 7.51 mmol) was added to TMAH (25% in water, 10.95 g, 30.04 mmol) at room temperature. The mixture was stirred for 24 hours, and was then cooled to 0° C. A mixture of 12M HCl (2.69 cm3, 32.1 mmol) and ice (3 g) was added and the mixture was extracted with CH2Cl2 (5×50 cm3). The extracts were evaporated under vacuum to give 2,2-bis(2-cyanoethyl)malonic acid (0.25 g, 15.8%) as a colorless very viscous oil (lit decomposed. 158° C.). was added the mixture was extracted with CH2Cl2 (5×50 cm3) The extracts were evaporated under vacuum

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of diethyl malonate (1 g, 6.2 mmol) and Triton B (40% in MeOH, 0.13 g, 0.31 mmol) in dioxane (1.2 cm3) was added dropwise acrylonitrile (0.658 g, 12.4 mmol) and the mixture was stirred at 60° C. overnight. The mixture was then cooled to room temperature and neutralized with 0.1 M HCl (3 cm3) and poured to ice-water (10 cm3). Crystals precipitated during 30 min. These were collected by filtration and recrystallised from EtOH (cooling in freezer before filtering off) to give diethyl 2,2-bis(2-cyanoethyl)malonate (1.25 g, 75.8%) as a white solid, mp 62.2-63.5° C. Crystals precipitated during 30 min These were collected by filtration recrystallised from EtOH (cooling in freezer before filtering off)