甘油烯丙基醚

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In a 2000 mL round bottom flask equipped with a large magnetic stir bar, 3-allyloxypropane-1,2-diol (5.94 g, 45 mmol), and tetrabutylammonium hydrogen sulfate (6 g, 18 mmol) were added. A solution of linoleyl mesylate (33.8 g, 98 mmol) in toluene (150 mL) was also made and added. The mixture was cooled to 0-5° C. with an ice bath. 50% sodium hydroxide (70 mL) was then slowly added, rinsing in with deionized water (20 mL). The resulting mixture is stirred at room temperature, under nitrogen for 40 hours. Deionized water (200 mL) and isopropyl acetate (200 mL) were added and the mixture stirred vigorously for a further 10-15 min. The mixture was transferred to a 1000-mL separating funnel and allowed to separate. The aqueous phase was removed and the organic phase washed with saturated sodium chloride solution (2×150 mL). The organic phase was dried with magnesium sulfate (40 g), filtered, and concentrated to obtain a neat orange oil. The oil was purified by column chromatography. Final yield: 19.5 g (69%). In a 2000 mL round bottom flask equipped with a large magnetic stir bar added rinsing in with deionized water (20 mL) Deionized water (200 mL) and isopropyl acetate (200 mL) were added the mixture stirred vigorously for a further 10-15 min separating funnel to separate The aqueous phase was removed the organic phase washed with saturated sodium chloride solution (2×150 mL) The organic phase was dried with magnesium sulfate (40 g) filtered concentrated to obtain a neat orange oil The oil was purified by column chromatography

反应条件: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In a 2000 mL round bottom flask equipped with a large magnetic stir bar, 3-allyloxypropane-1,2-diol (5.94 g, 45 mmol), and tetrabutylammonium hydrogen sulfate (6 g, 18 mmol) were added. A solution of linoleyl mesylate (33.8 g, 98 mmol) in toluene (150 mL) was also made and added. The mixture was cooled to 0-5° C. with an ice bath. 50% sodium hydroxide (70 mL) was then slowly added, rinsing in with deionized water (20 mL). The resulting mixture is stirred at room temperature, under nitrogen for 40 hours. Deionized water (200 mL) and isopropyl acetate (200 mL) were added and the mixture stirred vigorously for a further 10-15 min. The mixture was transferred to a 1000-mL separating funnel and allowed to separate. The aqueous phase was removed and the organic phase washed with saturated sodium chloride solution (2×150 mL). The organic phase was dried with magnesium sulfate (40 g), filtered, and concentrated to obtain a neat orange oil. The oil was purified by column chromatography. Final yield: 19.5 g (69%). In a 2000 mL round bottom flask equipped with a large magnetic stir bar added rinsing in with deionized water (20 mL) Deionized water (200 mL) and isopropyl acetate (200 mL) were added the mixture stirred vigorously for a further 10-15 min separating funnel to separate The aqueous phase was removed the organic phase washed with saturated sodium chloride solution (2×150 mL) The organic phase was dried with magnesium sulfate (40 g) filtered concentrated to obtain a neat orange oil The oil was purified by column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane was prepared by mixing acetone, 225 parts, 3-allyloxy-1,2propanediol, 195 parts and toluene, 480 parts in a flask fitted with a magnetic stirring bar and a water trap mounted with a reflux condenser. Concentrated sulfuric acid, 4 parts, was added to the flask and the mixture was heated to reflux. The first 170 parts of distillate were removed via the water trap, after which reflux was conducted and water was collected in the water trap. After 13 hours the reaction mixture was cooled, neutralized with solid sodium bicarbonate, distilled to remove water and toluene and then distilled under vacuum to give 161 parts of 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane having a boiling point of 57° to 58° at 4.5 Torr. The 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane was prepared fitted with a magnetic stirring bar and a water trap mounted with a reflux condenser the mixture was heated to reflux The first 170 parts of distillate were removed via the water trap after which reflux water was collected in the water trap After 13 hours the reaction mixture was cooled distilled to remove water and toluene distilled under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane was prepared by mixing acetone, 225 parts, 3-allyloxy-1,2propanediol, 195 parts and toluene, 480 parts in a flask fitted with a magnetic stirring bar and a water trap mounted with a reflux condenser. Concentrated sulfuric acid, 4 parts, was added to the flask and the mixture was heated to reflux. The first 170 parts of distillate were removed via the water trap, after which reflux was conducted and water was collected in the water trap. After 13 hours the reaction mixture was cooled, neutralized with solid sodium bicarbonate, distilled to remove water and toluene and then distilled under vacuum to give 161 parts of 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane having a boiling point of 57° to 58° at 4.5 Torr. The 4-allyloxymethyl-2,2-dimethyl-1,3-dioxolane was prepared fitted with a magnetic stirring bar and a water trap mounted with a reflux condenser the mixture was heated to reflux The first 170 parts of distillate were removed via the water trap after which reflux water was collected in the water trap After 13 hours the reaction mixture was cooled distilled to remove water and toluene distilled under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Benzene (250 ml) was added to 95% sodium hydride (11.4 g, 450.0 mmol), and the flask was flushed with nitrogen and sealed. A solution of 3-allyloxy-1,2-propanediol (6.6 g, 50.0 mmol) in benzene (75 ml) was added to the flask. Using a syringe, 97% 1-bromotetradecane (36.7 ml, 120.0 mmol) was added to the flask and the reaction was left to reflux overnight under a constant stream of nitrogen. Once cooled to room temperature, the excess sodium hydride was slowly quenched with ethanol until no further effervescence was observed. The solution was transferred to a separatory funnel with benzene (250 ml) and washed with distilled water (3×200 ml). The organic layer was dried with magnesium sulfate and the solvent removed on the rotary evaporator to yield a colourless oil. TLC (5% ether-hexane, developed in Molybdate) indicated that most of the starting material had reacted to form product. This resulting product was further purified by flash column chromatography (1-5% ether-hexane) to yield 15.0 g (57.3%) of 1,2-dimyristyloxy-3-allyloxypropane 1. the flask was flushed with nitrogen sealed the reaction was left to reflux overnight under a constant stream of nitrogen the excess sodium hydride was slowly quenched with ethanol until no further effervescence The solution was transferred to a separatory funnel with benzene (250 ml) washed with distilled water (3×200 ml) The organic layer was dried with magnesium sulfate the solvent removed on the rotary evaporator to yield a colourless oil had reacted to form product This resulting product was further purified by flash column chromatography (1-5% ether-hexane)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In the same polymerization reaction as used in Example 1, the polymerization by the procedure of Example 1 was carried out, except that 250 g of purified water, 410 g of an aqueous 35% sodium acrylate, and 140 g of an aqueous 40% solution of 3-allyloxy-1,2-dihydroxypropane monosulfate obtained by the reaction of 1 mole of 3-allyloxy-1,2-dihydroxypropane with 0.5 mole of sulfuric acid. The reaction produced a aqueous solution of a water-soluble copolymer (7). The conversion was 94% and the number-averaged molecular weight of the water-soluble copolymer (7) was 5,000. In the same polymerization reaction the polymerization by the procedure of Example 1

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: is formed when at room temperature, about 0.5 g (0.445 mL, 2.414 mmol, 1.1 equivalents) of tris(dimethylamino)arsine (TDMA), is added to about 10 mL dry hexane in a 25 mL round-bottom flask, and then about 0.29 g (0.27 mL, 2.19 mmol, 1.0 equivalents) of 3-(allyloxy)propane-1,2-diol is added dropwise into the system. The mixture is heated to reflux under nitrogen for about one hour, and then cooled to room temperature. Removal of the solvent in vacuum gives crude 4-((allyloxy)methyl)-N,N-dimethyl-1,3,2-dioxarsolan-2-amine as an oil. is formed when at room temperature The mixture is heated to reflux under nitrogen for about one hour Removal of the solvent in vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: is formed when at room temperature, about 0.5 g (0.445 mL, 2.414 mmol, 1.1 equivalents) of tris(dimethylamino)arsine (TDMA), is added to about 10 mL dry hexane in a 25 mL round-bottom flask, and then about 0.29 g (0.27 mL, 2.19 mmol, 1.0 equivalents) of 3-(allyloxy)propane-1,2-diol is added dropwise into the system. The mixture is heated to reflux under nitrogen for about one hour, and then cooled to room temperature. Removal of the solvent in vacuum gives crude 4-((allyloxy)methyl)-N,N-dimethyl-1,3,2-dioxarsolan-2-amine as an oil. is formed when at room temperature The mixture is heated to reflux under nitrogen for about one hour Removal of the solvent in vacuum

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Benzene (250 ml) was added to 95% sodium hydride (11.4 g, 450.0 mmol), and the flask was flushed with nitrogen and sealed. A solution of 3-allyloxy-1,2-propanediol (6.6 g, 50.0 mmol) in benzene (75 ml) was added to the flask. Using a syringe, 97% 1-bromotetradecane (36.7 ml, 120.0 mmol) was added to the flask and the reaction was left to reflux overnight under a constant stream of nitrogen. Once cooled to room temperature, the excess sodium hydride was slowly quenched with ethanol until no further effervescence was observed. The solution was transferred to a separatory funnel with benzene (250 ml) and washed with distilled water (3×200 ml). The organic layer was dried with magnesium sulfate and the solvent removed on the rotary evaporator to yield a colourless oil. TLC (5% ether-hexane, developed in Molybdate) indicated that most of the starting material had reacted to form product. This resulting product was further purified by flash column chromatography (1-5% ether-hexane) to yield 15.0 g (57.3%) of 1,2-dimyristyloxy-3-allyloxypropane 1. the flask was flushed with nitrogen sealed the reaction was left to reflux overnight under a constant stream of nitrogen the excess sodium hydride was slowly quenched with ethanol until no further effervescence The solution was transferred to a separatory funnel with benzene (250 ml) washed with distilled water (3×200 ml) The organic layer was dried with magnesium sulfate the solvent removed on the rotary evaporator to yield a colourless oil had reacted to form product This resulting product was further purified by flash column chromatography (1-5% ether-hexane)

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A 5,000 mL, 3-necked flask fitted with a mechanical stirrer, thermometer and 500 mL addition funnel was charged with water (2,000 mL) and 70% aqueous HClO4 (2.0 mL), then heated to 80° C. Allyl glycidyl ether (500 g, 4.38 mol) was added in one portion and the reaction mixture stirred for 12 hours. The mixture was neutralized by addition of 5% aqueous Na2CO3 to pH=8. The water was evaporated in vacuo to leave 550 g of crude product, which was distilled to yield 498 g (86%) of pure 3-allyloxy-1,2-propanediol: bp 76°-83° C. (0.4 mm). A 5,000 mL, 3-necked flask fitted with a mechanical stirrer thermometer and 500 mL addition funnel The water was evaporated in vacuo to leave 550 g of crude product, which was distilled