oxan-2-yl prop-2-enoate

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

Procedure: A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr. The mixture was washed with saturated aqueous sodium bicarbonate the organic layer was concentrated in vacuo The residue was distilled

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

Procedure: A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr. The mixture was washed with saturated aqueous sodium bicarbonate the organic layer was concentrated in vacuo The residue was distilled

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

Procedure: A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr. The mixture was washed with saturated aqueous sodium bicarbonate the organic layer was concentrated in vacuo The residue was distilled

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

Procedure: In 80 g of propylene glycol monomethyl ether were dissolved 78 g (0.5 mole) of tetrahydropyranyl acrylate and 42 g (0.5 mole) of methyl methacrylate, and 3 g of azobisisobutyronitrile was added thereto, after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C. After the polymerization, the reaction mixture was dropped into a large amount of water to coagulate a resin. The resin was recovered and dried in a vacuum drier kept at 50° C. overnight to obtain 96 g of a white fine powder of tetrahydropyranyl acrylate/methyl methacrylate copolymer resin. was added after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C After the polymerization The resin was recovered dried in a vacuum drier

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

Procedure: In 80 g of propylene glycol monomethyl ether were dissolved 78 g (0.5 mole) of tetrahydropyranyl acrylate and 42 g (0.5 mole) of methyl methacrylate, and 3 g of azobisisobutyronitrile was added thereto, after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C. After the polymerization, the reaction mixture was dropped into a large amount of water to coagulate a resin. The resin was recovered and dried in a vacuum drier kept at 50° C. overnight to obtain 96 g of a white fine powder of tetrahydropyranyl acrylate/methyl methacrylate copolymer resin. was added after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C After the polymerization The resin was recovered dried in a vacuum drier

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

Procedure: Using the procedure of Example 6, reaction of 10 g of poly(styrene [55 wt %], methyl acrylate [20 wt %], acrylic acid [25 wt %]) (Joncryl 67), 125 mL of 3,4-dihydro-2H-pyran, and 0.1 g of pyridine hydrochloride gave 10 g of poly(styrene, methyl acrylate, tetrahydropyranyl acrylate) after precipitation from dichloromethane in methanol at -70° C. 1H NMR (360 MHz, THF-d8): 5.9 (OCHO of tetrahydropyranyl ester). Mole ratio of styrene to tetrahydropyranyl ester=1.8:1. GPC: Mn=6260, Mw=15,900, Mw/Mn=2.54. DSC: Tg=52° C., decomposition endotherm peak at 180.77° C. (125.4 J/g). TGA: 20.69% weight loss at about 180° C. Titration of the product with 0.1N sodium hydroxide shows the presence of 0.2 meq/g of residual carboxylic acid groups. Titration of the starting material shows 3.4 meq/g of carboxylic acid.

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

Procedure: A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr. The mixture was washed with saturated aqueous sodium bicarbonate the organic layer was concentrated in vacuo The residue was distilled

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 310 mL (2.75 mol) of 3,4-dihydro-2H-pyran, 99.1 g (94 mL, 1.38 mol) of acrylic acid, 5 g of crosslinked poly(4-vinylpyridine hydrochloride) (Fluka Chemical Corp., catalog number 82803, 6 meq/g), and 0.5 g of phenothiazine was warmed until an exothermic reaction caused the temperature to rise to 99° C. An ice bath was used to cool the mixture to 65° C., and the mixture was stirred at 65° C. for 18 hours. After cooling to room temperature, the mixture was filtered to remove the catalyst. NMR analysis of the filtrate showed the presence of 2-tetrahydropyranyl acrylate and 3,4-dihydro-2H-pyran with little or no acrylic acid. The mixture was stirred with anhydrous sodium carbonate and calcium hydride for 1 hour. After removal of excess 3,4-dihydro-2H-pyran in a rotary evaporator, distillation over calcium hydride, anhydrous sodium carbonate, and phenothiazine gave 136.6 g of 2-tetrahydropyranyl acrylate, b.p. 66°-70° C. (3.2 mm). was warmed until an exothermic reaction to rise to 99° C An ice bath was used After cooling to room temperature the mixture was filtered to remove the catalyst The mixture was stirred with anhydrous sodium carbonate and calcium hydride for 1 hour After removal of excess 3,4-dihydro-2H-pyran in a rotary evaporator, distillation over calcium hydride, anhydrous sodium carbonate, and phenothiazine

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

Procedure: A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr. The mixture was washed with saturated aqueous sodium bicarbonate the organic layer was concentrated in vacuo The residue was distilled

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

Procedure: A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr. The mixture was washed with saturated aqueous sodium bicarbonate the organic layer was concentrated in vacuo The residue was distilled

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

Procedure: A solution of 10.5 g (146 mmol, 10 ml) acrylic acid and 14.0 g (166 mmol, 15.2 ml) dihydropyran in 40 ml dichloromethane was stirred at room temperature for one day. The mixture was washed with saturated aqueous sodium bicarbonate and the organic layer was concentrated in vacuo. The residue was distilled to give 5.93 g (38.0 mmol, 26% yield) tetrahydropyran-2-yl acrylate, bp 40° C. at 0.2 torr. The mixture was washed with saturated aqueous sodium bicarbonate the organic layer was concentrated in vacuo The residue was distilled

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

Procedure: In 80 g of propylene glycol monomethyl ether were dissolved 78 g (0.5 mole) of tetrahydropyranyl acrylate and 42 g (0.5 mole) of methyl methacrylate, and 3 g of azobisisobutyronitrile was added thereto, after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C. After the polymerization, the reaction mixture was dropped into a large amount of water to coagulate a resin. The resin was recovered and dried in a vacuum drier kept at 50° C. overnight to obtain 96 g of a white fine powder of tetrahydropyranyl acrylate/methyl methacrylate copolymer resin. was added after which they were subjected to polymerization for 10 hours under a nitrogen atmosphere while the reaction temperature was kept at 80° C After the polymerization The resin was recovered dried in a vacuum drier