1,4-dioxan-2-ylmethanol

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

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

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

Procedure: The title compound was synthesized as described for Intermediate example I-81 in 58% yield starting from ethyl 6-chloronicotinate and 1,4-dioxan-2-ylmethanol. The reduction was performed using 3 equiv of lithium hydroxide. The final aqueous solution was extracted with ethyl acetate in order to collect the product; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.70 (d, 1 H), 8.14 (dd, 1 H), 6.93 (d, 1 H), 4.28-4.32 (m, 2 H), 3.84-3.92 (m, 1 H), 3.72-3.83 (m, 2 H), 3.56-3.69 (m, 2 H), 3.44-3.55 (m, 1 H), 3.35-3.42 (m, 1 H); S (ESI) m/z 240[M+H+], m/z 238[M−H+]; The final aqueous solution was extracted with ethyl acetate in order to collect the product

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

Procedure: The title compound was synthesized as described for Intermediate example I-81 in 58% yield starting from ethyl 6-chloronicotinate and 1,4-dioxan-2-ylmethanol. The reduction was performed using 3 equiv of lithium hydroxide. The final aqueous solution was extracted with ethyl acetate in order to collect the product; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.70 (d, 1 H), 8.14 (dd, 1 H), 6.93 (d, 1 H), 4.28-4.32 (m, 2 H), 3.84-3.92 (m, 1 H), 3.72-3.83 (m, 2 H), 3.56-3.69 (m, 2 H), 3.44-3.55 (m, 1 H), 3.35-3.42 (m, 1 H); S (ESI) m/z 240[M+H+], m/z 238[M−H+]; The final aqueous solution was extracted with ethyl acetate in order to collect the product

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

Procedure: Following the procedure of Example 2, a mixture of 172 grams (1.0 mole) of cyclohexane dicarboxylic acid, 265.5 grams (2.25 moles) of 1,4-dioxanemethanol, 75 milliliters of xylene and 0.3 gram of dibutyltin oxide catalyst yields a gray waxy product in 91 percent yield. Recrystallization from an ethanol-water mixture gives the colorless bis-1,4-dioxanemethanol cyclohexanedicarboxylate. yields a gray waxy product in 91 percent yield Recrystallization from an ethanol-water mixture

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

Procedure: Following the procedure of Example 2, a mixture of 172 grams (1.0 mole) of cyclohexane dicarboxylic acid, 265.5 grams (2.25 moles) of 1,4-dioxanemethanol, 75 milliliters of xylene and 0.3 gram of dibutyltin oxide catalyst yields a gray waxy product in 91 percent yield. Recrystallization from an ethanol-water mixture gives the colorless bis-1,4-dioxanemethanol cyclohexanedicarboxylate. yields a gray waxy product in 91 percent yield Recrystallization from an ethanol-water mixture

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

Procedure: Following the procedure of Example 2, a mixture of 87.1 grams (0.5 mole) of sebacic acid, 146.5 grams (1.25 moles) of 1,4-dioxanemethanol, 50 milliliters of toluene and 0.2 gram of dibutyltin dilaurate catalyst yields a waxy product in 87 percent yield which is recrystallized from an isopropanol-water mixture to give the colorless bis-1,4-dioxanemethanol sebacate. yields a waxy product in 87 percent yield which is recrystallized from an isopropanol-water mixture

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

Procedure: Following the procedure of Example 2, a mixture of 98 grams (1 mole) of maleic anhydride, 354 grams (3.0 moles) of 1,4-dioxanemethanol and 50 milliliters of benzene affords an 82 percent yield of bis-1,4-dioxanemethanol maleate.

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

Procedure: Following the procedure of Example 2, a mixture of 98 grams (1 mole) of maleic anhydride, 354 grams (3.0 moles) of 1,4-dioxanemethanol and 50 milliliters of benzene affords an 82 percent yield of bis-1,4-dioxanemethanol maleate.

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

Procedure: Following the procedure of Example 2, a mixture of 166 grams (1 mole) of isophthalic acid, 295 grams (2.5 moles) of 1,4-dioxanemethanol, 100 milliliters of benzene and 0.1 gram of p-toluenesulfonic acid catalyst gives an 86 percent yield of the white, waxy bis-1,4-dioxanemethanol isophthalate.

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

Procedure: (1,4-Dioxan-2-yl)methanol (380 mg) in tetrahydrofuran (30 ml) was treated with sodium hydride (60%) (245 mg) at room temperature for 30 minutes. The reaction mixture was cooled in an ice bath and 4-fluoro-3-nitrobenzenesulfonamide (675 mg) was added. The resulting mixture was stirred at room temperature for 2 hours and another portion of sodium hydride (60%, 245 mg) was added. The reaction mixture was stirred overnight and quenched with ice water (3 ml). The cloudy mixture was filtered and the filtrate was concentrated. The residue was triturated with methanol to give the title compound. The reaction mixture was cooled in an ice bath The reaction mixture was stirred overnight quenched with ice water (3 ml) The cloudy mixture was filtered the filtrate was concentrated The residue was triturated with methanol

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

Procedure: (1,4-Dioxan-2-yl)methanol (380 mg) in tetrahydrofuran (30 ml) was treated with sodium hydride (60%) (245 mg) at room temperature for 30 minutes. The reaction mixture was cooled in an ice bath and 4-fluoro-3-nitrobenzenesulfonamide (675 mg) was added. The resulting mixture was stirred at room temperature for 2 hours and another portion of sodium hydride (60%, 245 mg) was added. The reaction mixture was stirred overnight and quenched with ice water (3 ml). The cloudy mixture was filtered and the filtrate was concentrated. The residue was triturated with methanol to give the title compound. The reaction mixture was cooled in an ice bath The reaction mixture was stirred overnight quenched with ice water (3 ml) The cloudy mixture was filtered the filtrate was concentrated The residue was triturated with methanol