butane-1,2-diol

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

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

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

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: To a mixture of 0.34 g of optically active 1,2-butanediol, 5 ml of toluene and 2.5 ml of pyridine, 1.2 g of acetyl chloride was added dropwise in an ice bath and stirred for two hours. 10 ml of water and 10 ml of toluene were added to the reaction mixture and stirred. The obtained solution was washed with 2N sodium hydroxide and then with water. The toluene solution dried over anhydrous magnesium sulfate. Toluene was distilled away from the solution under reduced pressure, the residue was purified with a chromatograph over silica gel, and 1,2-butanediol diacetate was obtained. The obtained compound had a gas chromatographic purity of 95.0%. It showed a specific rotation of [α]D30 +14.8(c=1.12, CHCl3). was added dropwise in an ice bath stirred The obtained solution was washed with 2N sodium hydroxide The toluene solution dried over anhydrous magnesium sulfate Toluene was distilled away from the solution under reduced pressure the residue was purified with a chromatograph over silica gel

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

Procedure: To a mixture of 0.34 g of optically active 1,2-butanediol, 5 ml of toluene and 2.5 ml of pyridine, 1.2 g of acetyl chloride was added dropwise in an ice bath and stirred for two hours. 10 ml of water and 10 ml of toluene were added to the reaction mixture and stirred. The obtained solution was washed with 2N sodium hydroxide and then with water. The toluene solution dried over anhydrous magnesium sulfate. Toluene was distilled away from the solution under reduced pressure, the residue was purified with a chromatograph over silica gel, and 1,2-butanediol diacetate was obtained. The obtained compound had a gas chromatographic purity of 95.0%. It showed a specific rotation of [α]D30 +14.8(c=1.12, CHCl3). was added dropwise in an ice bath stirred The obtained solution was washed with 2N sodium hydroxide The toluene solution dried over anhydrous magnesium sulfate Toluene was distilled away from the solution under reduced pressure the residue was purified with a chromatograph over silica gel

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

Procedure: To the mixture of 0.48 g of optically active 1,2-butanediol, 5 ml of toluene and 2.5 ml of pyridine, 1.7 g of acetyl chloride was added dropwise in an ice bath and stirred for two hours. 10 ml of water and 10 ml of toluene were added to the reaction mixture and stirred. The obtained solution was washed with 2N sodium hydroxide and then with water. The toluene solution was dried over anhydrous magnesium sulfate. Toluene was distilled away from the solution under reduced pressure, the residue was purified with a chromatograph over silica gel, and 1,2-butanediol diacetate was obtained. The obtained compound had a gas chromatographic purity of 98.9%. It showed a specific rotation of [α]D28 =-12.2° C. (c=1.08, CHCl3). The optical purity of the compound was determined by using a column of optical resolution (Trade name: Chiral Cel OB, produced by Daicel Chemical Industries, Ltd., in Japan). From the peak area of the product, the optical purity was 85% ee. was added dropwise in an ice bath stirred The obtained solution was washed with 2N sodium hydroxide The toluene solution was dried over anhydrous magnesium sulfate Toluene was distilled away from the solution under reduced pressure the residue was purified with a chromatograph over silica gel

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

Procedure: To the mixture of 0.48 g of optically active 1,2-butanediol, 5 ml of toluene and 2.5 ml of pyridine, 1.7 g of acetyl chloride was added dropwise in an ice bath and stirred for two hours. 10 ml of water and 10 ml of toluene were added to the reaction mixture and stirred. The obtained solution was washed with 2N sodium hydroxide and then with water. The toluene solution was dried over anhydrous magnesium sulfate. Toluene was distilled away from the solution under reduced pressure, the residue was purified with a chromatograph over silica gel, and 1,2-butanediol diacetate was obtained. The obtained compound had a gas chromatographic purity of 98.9%. It showed a specific rotation of [α]D28 =-12.2° C. (c=1.08, CHCl3). The optical purity of the compound was determined by using a column of optical resolution (Trade name: Chiral Cel OB, produced by Daicel Chemical Industries, Ltd., in Japan). From the peak area of the product, the optical purity was 85% ee. was added dropwise in an ice bath stirred The obtained solution was washed with 2N sodium hydroxide The toluene solution was dried over anhydrous magnesium sulfate Toluene was distilled away from the solution under reduced pressure the residue was purified with a chromatograph over silica gel

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

Procedure: To a stirred solution of 74.4 parts of 2-bromo-1-(2-naphthalenyl)-1-ethanone in 240 parts of butanol are added successively 3 parts of 4-methylbenzenesulfonic acid and 270 parts of benzene. Then there are added dropwise 28 parts of 1,2-butanediol. Upon completion, stirring is continued overnight at reflux temperature. The reaction mixture is evaporated. The residue is dissolved in 2,2'-oxybispropane and the solution is stirred with a diluted sodium hydroxide solution. The layers are separated and the aqueous phase is extracted with 2,2'-oxybispropane. The extract is neutralized with water, dried, filtered and evaporated. The oily residue is crystallized from methanol. The product is filtered off and recrystallized from methanol, yielding 41 parts of 2-(bromomethyl)-2-(2-naphthalenyl)-1,3-dioxolane; mp. 64° C. at reflux temperature The reaction mixture is evaporated The residue is dissolved in 2,2'-oxybispropane the solution is stirred with a diluted sodium hydroxide solution The layers are separated the aqueous phase is extracted with 2,2'-oxybispropane dried filtered evaporated The oily residue is crystallized from methanol The product is filtered off recrystallized from methanol

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

Procedure: To a stirred solution of 74.4 parts of 2-bromo-1-(2-naphthalenyl)-1-ethanone in 240 parts of butanol are added successively 3 parts of 4-methylbenzenesulfonic acid and 270 parts of benzene. Then there are added dropwise 28 parts of 1,2-butanediol. Upon completion, stirring is continued overnight at reflux temperature. The reaction mixture is evaporated. The residue is dissolved in 2,2'-oxybispropane and the solution is stirred with a diluted sodium hydroxide solution. The layers are separated and the aqueous phase is extracted with 2,2'-oxybispropane. The extract is neutralized with water, dried, filtered and evaporated. The oily residue is crystallized from methanol. The product is filtered off and recrystallized from methanol, yielding 41 parts of 2-(bromomethyl)-2-(2-naphthalenyl)-1,3-dioxolane; mp. 64° C. at reflux temperature The reaction mixture is evaporated The residue is dissolved in 2,2'-oxybispropane the solution is stirred with a diluted sodium hydroxide solution The layers are separated the aqueous phase is extracted with 2,2'-oxybispropane dried filtered evaporated The oily residue is crystallized from methanol The product is filtered off recrystallized from methanol

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

Procedure: Investigations into the PCR enhancing capabilities of diol cosolvents were carried out using GTP as the primary template. This choice was made in order to provide the cosolvents with the greatest opportunity to demonstrate their effectiveness because GTP has the lowest GC content of the three templates used. Whether any diol is exclusively capable of amplifying c-jun at 92° C. was not investigated, since the diol family does not contain any member analogous to tetramethylene sulfoxide or sulfolane. The standard protocol for annealing temperature and concentration gradient screening was again followed. Additives were tested with GTP over annealing temperature gradients using a 95° C. denaturing temperature; 1,2-pentanediol and 1,2-hexanediol displayed detectable amplification only in very narrow concentration ranges, and trans-1,2-cyclopentanediol was inhibitory at all concentrations. These cosolvents were thus omitted from further studies. The optimal annealing temperatures for the remaining compounds were: ethylene glycol, 1,2-propanediol, 1,3-propanediol and cis-1,2-cyclopentanediol—58° C.; 1,2-butanediol—54° C.; 1,3-butanediol and 1,4-butanediol—60° C.; 2,4-pentanediol, 1,5-pentanediol, 1,6-hexanediol and MPD—56° C. The following concentration gradients were tested at these annealing temperatures: ethylene glycol—0.5, 1.0, 1.5, 2.0, 2.5, 3.0 and 4.5M; 1,2-propanediol—0.3, 0.5, 0.7, 0.9, 1.1, 1.4, 1.6, 1.8 and 2.0M; 1,3-propanediol—0.3, 0.5, 0.7, 0.9, 1.1 and 1.4M; 1,2-butanediol—0.1, 0.3, 0.5, 0.7, 0.8, 0.9 and 1.1M; 1,3-butanediol—0.2, 0.4, 0.5, 0.6, 0.7, 0.8, 1.0 and 1.1M; 1,4-butanediol—0.2, 0.4, 0.5, 0.6, 0.7, 0.8 and 1.0M; 1,5-pentanediol—0.1 to 0.6M in 0.1M intervals; 2,4-pentanediol—0.1 to 0.6 in 0.1M intervals; 1,6-hexanediol—0.05 to 0.35M in 0.05M intervals; MPD—0.1 to 0.5M in 0.1M intervals; cis-1,2-cyclopentanediol—0.05 to 0.3M in 0.05M intervals; glycerol—0.1 to 1.3M in 0.2M intervals. FIG. 4 shows results from the concentration gradients for 1,2-butanediol, 1,2-propanediol and glycerol. Potencies and effective ranges of the cosolvents are listed in Table 1. Virtually every diol studied provided nearly 100% specificity with GTP; thus, specificities are omitted from the table. Variation of amplification with concentration is displayed for 1,2-propanediol, 1,4-butanediol, 1,5-pentanediol and glycerol in FIG. 5. Splines for the three isomeric butanediols are shown in FIG. 6. to provide the cosolvents with the greatest opportunity is exclusively capable of amplifying c-jun at 92° C. The standard protocol for annealing temperature and concentration gradient screening using a 95° C. 1,2-pentanediol and 1,2-hexanediol displayed detectable amplification only in very narrow concentration ranges, and trans-1,2-cyclopentanediol was inhibitory at all concentrations ethylene glycol, 1,2-propanediol, 1,3-propanediol and cis-1,2-cyclopentanediol—58° C. 1,2-butanediol—54° C. 1,3-butanediol and 1,4-butanediol—60° C. 2,4-pentanediol, 1,5-pentanediol, 1,6-hexanediol and MPD—56° C The following concentration gradients