decan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g). Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet The mineral oil is removed by washing with hexanes Anhydrous dimethyl sulfoxide (500 ml) is added to the flask The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran slowly added to the reaction mixture thru the dropping funnel the reaction at 25-30° C is slowly added thru a dropping funnel Reaction cooling to maintain 25-30° C and then poured into a separatory funnel After shaking the oil phase (top) to separate out the water phase is removed The extractions of the oil phase The organic phase is collected vacuum distilled purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran. (6-hydroxyhexyl)triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g). Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet The mineral oil is removed by washing with hexanes Anhydrous dimethyl sulfoxide (500 ml) is added to the flask The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran slowly added to the reaction mixture thru the dropping funnel the reaction at 25-30° C is slowly added thru a dropping funnel Reaction cooling to maintain 25-30° C and then poured into a separatory funnel After shaking the oil phase (top) to separate out the water phase is removed The extractions of the oil phase The organic phase is collected vacuum distilled purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran. (6-hydroxyhexyl)triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g). Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet The mineral oil is removed by washing with hexanes Anhydrous dimethyl sulfoxide (500 ml) is added to the flask The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran slowly added to the reaction mixture thru the dropping funnel the reaction at 25-30° C is slowly added thru a dropping funnel Reaction cooling to maintain 25-30° C and then poured into a separatory funnel After shaking the oil phase (top) to separate out the water phase is removed The extractions of the oil phase The organic phase is collected vacuum distilled purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a dried 5L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g). Into a dried 5L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet The mineral oil is removed by washing with hexanes Anhydrous dimethyl sulfoxide (500 ml) is added to the flask The reaction mixture is cooled to room temperature followed by addition of 1L of anhydrous tetrahydrofuran slowly added to the reaction mixture thru the dropping funnel the reaction at 25-30° C is slowly added thru a dropping funnel Reaction cooling to maintain 25-30° C and then poured into a separatory funnel After shaking the oil phase (top) to separate out the water phase is removed The extractions of the oil phase The organic phase is collected vacuum distilled purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a dried 5L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g). Into a dried 5L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet The mineral oil is removed by washing with hexanes Anhydrous dimethyl sulfoxide (500 ml) is added to the flask The reaction mixture is cooled to room temperature followed by addition of 1L of anhydrous tetrahydrofuran slowly added to the reaction mixture thru the dropping funnel the reaction at 25-30° C is slowly added thru a dropping funnel Reaction cooling to maintain 25-30° C and then poured into a separatory funnel After shaking the oil phase (top) to separate out the water phase is removed The extractions of the oil phase The organic phase is collected vacuum distilled purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet, dropping funnel, thermometer and nitrogen outlet is added 80 g of 60% sodium hydride (2.0 mol) in mineral oil. The mineral oil is removed by washing with hexanes. Anhydrous dimethyl sulfoxide (500 ml) is added to the flask and heated to 70° C. until evolution of hydrogen stops. The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran. (6-hydroxyhexyl) triphenylphosphonium bromide (443.4 g, 1 mol) is slurried with warm anhydrous dimethyl sulfoxide (50° C., 500 ml) and slowly added to the reaction mixture thru the dropping funnel while keeping the reaction at 25-30° C. The reaction is stirred for 30 minutes at room temperature at which time 2-decanone (171.9 g, 1.1 mol) is slowly added thru a dropping funnel. Reaction is slightly exothermic and cooling is needed to maintain 25-30° C. Mixture is stirred for 18 hrs. and then poured into a separatory funnel containing 600 ml of purified water and 300 ml of hexanes. After shaking the oil phase (top) is allowed to separate out and the water phase is removed. The extractions of the oil phase are continued using water until both phases are clear. The organic phase is collected, vacuum distilled and purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase) to obtain a clear, oily product (119.1 g). Into a dried 5 L, 3 neck round bottom flask fitted with mechanical stirring, nitrogen inlet The mineral oil is removed by washing with hexanes Anhydrous dimethyl sulfoxide (500 ml) is added to the flask The reaction mixture is cooled to room temperature followed by addition of 1 L of anhydrous tetrahydrofuran slowly added to the reaction mixture thru the dropping funnel the reaction at 25-30° C is slowly added thru a dropping funnel Reaction cooling to maintain 25-30° C and then poured into a separatory funnel After shaking the oil phase (top) to separate out the water phase is removed The extractions of the oil phase The organic phase is collected vacuum distilled purified by liquid chromatography (90:10 hexanes:ethyl acetate, silica gel stationary phase)

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

Procedure: Prepared from glyoxylic acid (5.10 g, 6.7 mmol), 2-decanone (15.0 g, 9.6 mmol) and orthophosphoric acid (20 ml). νmax 2925, 2820, 1690, 1460, 1380, 1240, 1120, 880, 720 cm−1. 1H n.m.r. δ (CDCl3) 0.87, t J 7.2 Hz, 3H, CH3; 1.29, m, 10H, CH2; 2.39, s, 3H, CH3; 2.77, t J 6.8 Hz, 2H, CH2; 6.50, s, CH. 13C n.m.r. δ (CDCl3): 13.9, CH3; 22.5, 26.6, 26.9, 29.1, 29.6, 31.6 CH2; 28.8, CH3; 124.3, C2; 157.9, C3; 170.9, COOH; 199.9 C2.

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

Procedure: Prepared from glyoxylic acid (5.10 g, 6.7 mmol), 2-decanone (15.0 g, 9.6 mmol) and orthophosphoric acid (20 ml). νmax 2925, 2820, 1690, 1460, 1380, 1240, 1120, 880, 720 cm−1. 1H n.m.r. δ (CDCl3) 0.87, t J 7.2 Hz, 3H, CH3; 1.29, m, 10H, CH2; 2.39, s, 3H, CH3; 2.77, t J 6.8 Hz, 2H, CH2; 6.50, s, CH. 13C n.m.r. δ (CDCl3): 13.9, CH3; 22.5, 26.6, 26.9, 29.1, 29.6, 31.6 CH2; 28.8, CH3; 124.3, C2; 157.9, C3; 170.9, COOH; 199.9 C2.

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

Procedure: 3-decanol and 4-decanol (1.10 mmol); 2-decanone (1.73 mmol); 3-decanone and 4-decanone (1.41 mmol).

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

Procedure: 3-decanol and 4-decanol (1.10 mmol); 2-decanone (1.73 mmol); 3-decanone and 4-decanone (1.41 mmol).