hexane-1,2,6-triol

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

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

Procedure: 13.4 g of commercial 1,2,6-hexanetriol are added to 12.4 ml of diethoxymethane and the mixture is refluxed in the presence of 500 mg of toluenesulfonic acid acting as a transacetalisation catalyst. The ethanol is evaporated at 80° C. and the 4-(4-hydroxybutyl)-1,2-dioxolane obtained is purified by distillation. 7.3 g of this product and 4.6 g of epichlorhydrine are reacted in the presence of 2.8 g of potassium hydroxide (powder) and tetrabutylammonium chloride, to form the monomer 4-[(4-glycidyloxy)-butyl]-1,3-dioxolane The ethanol is evaporated at 80° C.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2,6-trihydroxyhexane (10.0 g, 74.6 mmol) and benzaldehyde dimethylacetal (15.0 g, 98.7 mmol) in dry DMF (10 mL) was added Amberlyst 15 (5.0 g). The mixture was stirred at 100° C. for 5 min, then cooled and filtered. The filtrate was concentrated and residue obtained was re-dissolved in ethyl acetate. After being washed with water and brine, the solution was dried over Na2SO4. The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate. Concentration of the proper fractions afforded 11.0 g (66%) of the title product (a mixture of diastereomers) as a colorless oil: 1H NMR (CDCl3, 300 MHz, ppm) 7.48 (m, 2H), 7.39 (m, 3H), 5.92 (s, 0.4H), 5.80 (s, 0.6H), 4.3-4.1 (m, 2H), 3.64 (m, 3H), 1.8-1.4 (m, 6H). cooled filtered The filtrate was concentrated residue obtained After being washed with water and brine the solution was dried over Na2SO4 The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate

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

Procedure: 13.4 g of commercial 1,2,6-hexanetriol are added to 12.4 ml of diethoxymethane and the mixture is refluxed in the presence of 500 mg of toluenesulfonic acid acting as a transacetalisation catalyst. The ethanol is evaporated at 80° C. and the 4-(4-hydroxybutyl)-1,2-dioxolane obtained is purified by distillation. 7.3 g of this product and 4.6 g of epichlorhydrine are reacted in the presence of 2.8 g of potassium hydroxide (powder) and tetrabutylammonium chloride, to form the monomer 4-[(4-glycidyloxy)-butyl]-1,3-dioxolane The ethanol is evaporated at 80° C.

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

Procedure: 13.4 g of commercial 1,2,6-hexanetriol are added to 12.4 ml of diethoxymethane and the mixture is refluxed in the presence of 500 mg of toluenesulfonic acid acting as a transacetalisation catalyst. The ethanol is evaporated at 80° C. and the 4-(4-hydroxybutyl)-1,2-dioxolane obtained is purified by distillation. 7.3 g of this product and 4.6 g of epichlorhydrine are reacted in the presence of 2.8 g of potassium hydroxide (powder) and tetrabutylammonium chloride, to form the monomer 4-[(4-glycidyloxy)-butyl]-1,3-dioxolane The ethanol is evaporated at 80° C.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2,6-trihydroxyhexane (10.0 g, 74.6 mmol) and benzaldehyde dimethylacetal (15.0 g, 98.7 mmol) in dry DMF (10 mL) was added Amberlyst 15 (5.0 g). The mixture was stirred at 100° C. for 5 min, then cooled and filtered. The filtrate was concentrated and residue obtained was re-dissolved in ethyl acetate. After being washed with water and brine, the solution was dried over Na2SO4. The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate. Concentration of the proper fractions afforded 11.0 g (66%) of the title product (a mixture of diastereomers) as a colorless oil: 1H NMR (CDCl3, 300 MHz, ppm) 7.48 (m, 2H), 7.39 (m, 3H), 5.92 (s, 0.4H), 5.80 (s, 0.6H), 4.3-4.1 (m, 2H), 3.64 (m, 3H), 1.8-1.4 (m, 6H). cooled filtered The filtrate was concentrated residue obtained After being washed with water and brine the solution was dried over Na2SO4 The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate

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

Procedure: 9.06 g (45.2 mmol) of 3,4-di-n-propoxythiophene, 30.3 g (226 mmol) of 1,2,6-hexanetriol and 0.09 g (0.5 mmol) of p-toluenesulphonic acid are heated to 150 to 165° C. (bath temperature) under N2 for 3 h. During this time, 5.8 g of distillate (substantially n-propanol) were collected. The cooled liquid was diluted with 50 ml of methylene chloride, washed to neutrality and to free it of hexanetriol with water and the organic phase was dried over Na2SO4. After filtering and evaporating the methylene chloride, the residue (6.73 g=74.8% of theory) was identified by 1H NMR spectroscopy (in CDCl3 against TMS) using δ=6.30 ppm (2H, thiophene H) and 2.85 ppm (1H, OH) as being substantially 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)-1-butanol. During this time, 5.8 g of distillate (substantially n-propanol) were collected The cooled liquid was diluted with 50 ml of methylene chloride washed to neutrality the organic phase was dried over Na2SO4 After filtering evaporating the methylene chloride

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,2,6-trihydroxyhexane (10.0 g, 74.6 mmol) and benzaldehyde dimethylacetal (15.0 g, 98.7 mmol) in dry DMF (10 mL) was added Amberlyst 15 (5.0 g). The mixture was stirred at 100° C. for 5 min, then cooled and filtered. The filtrate was concentrated and residue obtained was re-dissolved in ethyl acetate. After being washed with water and brine, the solution was dried over Na2SO4. The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate. Concentration of the proper fractions afforded 11.0 g (66%) of the title product (a mixture of diastereomers) as a colorless oil: 1H NMR (CDCl3, 300 MHz, ppm) 7.48 (m, 2H), 7.39 (m, 3H), 5.92 (s, 0.4H), 5.80 (s, 0.6H), 4.3-4.1 (m, 2H), 3.64 (m, 3H), 1.8-1.4 (m, 6H). cooled filtered The filtrate was concentrated residue obtained After being washed with water and brine the solution was dried over Na2SO4 The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate

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

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

Procedure: 9.06 g (45.2 mmol) of 3,4-di-n-propoxythiophene, 30.3 g (226 mmol) of 1,2,6-hexanetriol and 0.09 g (0.5 mmol) of p-toluenesulphonic acid are heated to 150 to 165° C. (bath temperature) under N2 for 3 h. During this time, 5.8 g of distillate (substantially n-propanol) were collected. The cooled liquid was diluted with 50 ml of methylene chloride, washed to neutrality and to free it of hexanetriol with water and the organic phase was dried over Na2SO4. After filtering and evaporating the methylene chloride, the residue (6.73 g=74.8% of theory) was identified by 1H NMR spectroscopy (in CDCl3 against TMS) using δ=6.30 ppm (2H, thiophene H) and 2.85 ppm (1H, OH) as being substantially 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)-1-butanol. During this time, 5.8 g of distillate (substantially n-propanol) were collected The cooled liquid was diluted with 50 ml of methylene chloride washed to neutrality the organic phase was dried over Na2SO4 After filtering evaporating the methylene chloride

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

Procedure: To a stirred solution of 1,2,6-hexanetriol (10.0 g, 74.6 mmol) in acetone (50 ml) was added dichloromethane (50 ml), p-toluene sulphonic acid (1 mol %, catalyst) and anhydrous magnesium sulphate (50 g). The mixture was allowed to stir at ambient temperature for 24 hours. The MgSO4 was then removed via filtration and the acetone/dichloromethane solution washed with saturated sodium bicarbonate solution (1×30 ml) and water (2×30 ml). The organic solution was then dried over anhydrous MgSO4, filtered and solvent removed in vacuo, to yield the product as a colourless liquid. Yield=13.0 g (79%). The MgSO4 was then removed via filtration the acetone/dichloromethane solution washed with saturated sodium bicarbonate solution (1×30 ml) and water (2×30 ml) The organic solution was then dried over anhydrous MgSO4 filtered solvent removed in vacuo

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

Procedure: To a stirred solution of 1,2,6-hexanetriol (10.0 g, 74.6 mmol) in acetone (50 ml) was added dichloromethane (50 ml), p-toluene sulphonic acid (1 mol %, catalyst) and anhydrous magnesium sulphate (50 g). The mixture was allowed to stir at ambient temperature for 24 hours. The MgSO4 was then removed via filtration and the acetone/dichloromethane solution washed with saturated sodium bicarbonate solution (1×30 ml) and water (2×30 ml). The organic solution was then dried over anhydrous MgSO4, filtered and solvent removed in vacuo, to yield the product as a colourless liquid. Yield=13.0 g (79%). The MgSO4 was then removed via filtration the acetone/dichloromethane solution washed with saturated sodium bicarbonate solution (1×30 ml) and water (2×30 ml) The organic solution was then dried over anhydrous MgSO4 filtered solvent removed in vacuo