3-dodecoxypropane-1,2-diol

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

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

Procedure: Isopropylidineglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powdered KOH (22.4 g, 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromodecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 hours. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution was refluxed for 16 hours. After cooling, ice water (150 mL) was added, and the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol), 71% of a white solid. The resulting mixture was refluxed for 4 hours the solution was refluxed for 10 hours After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution was refluxed for 16 hours After cooling ice water (150 mL) was added the layers were separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Procedure: Isopropylideneglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powered KOH (22.4 g, 0.04 mol) in 150 mL of toluene. The resulting mixture was refluxed for 4 h. 1-Bromododecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 h. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution refluxed for 16 h. After cooling, ice-water (150 mL) was addecl, and the layers separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol, 71%) of a white solid. The resulting mixture was refluxed for 4 h the solution was refluxed for 10 h After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution refluxed for 16 h After cooling the layers separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Procedure: Isopropylidineglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powdered KOH (22.4 g, 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromodecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 hours. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution was refluxed for 16 hours. After cooling, ice water (150 mL) was added, and the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol), 71% of a white solid. The resulting mixture was refluxed for 4 hours the solution was refluxed for 10 hours After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution was refluxed for 16 hours After cooling ice water (150 mL) was added the layers were separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Procedure: Isopropylidineglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powdered KOH (22.4 g, 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromodecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 hours. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution was refluxed for 16 hours. After cooling, ice water (150 mL) was added, and the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol), 71% of a white solid. The resulting mixture was refluxed for 4 hours the solution was refluxed for 10 hours After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution was refluxed for 16 hours After cooling ice water (150 mL) was added the layers were separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Procedure: Isopropylideneglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powered KOH (22.4 g, 0.04 mol) in 150 mL of toluene. The resulting mixture was refluxed for 4 h. 1-Bromododecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 h. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution refluxed for 16 h. After cooling, ice-water (150 mL) was addecl, and the layers separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol, 71%) of a white solid. The resulting mixture was refluxed for 4 h the solution was refluxed for 10 h After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution refluxed for 16 h After cooling the layers separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Conditions: temp:200.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an autoclave, 249 of the resulting dodecyl glycidyl ether, 97.2 g of water and 34.8 g of sodium bicarbonate were charged and were stirred at 200° C. for 8 hours. After completion of the reaction, the reaction mixture was dehydrated at 120° C. under reduced pressure (6.67 kPa), followed by purification by distillation under reduced pressure (13 to 26 Pa, 160 to 170° C.), whereby 117 g of monododecyl glyceryl ether was obtained. As a result of gas chromatographic analysis (hereinafter abbreviated as “GLC”), it was found that the resulting product had a purity not less than 99% and the content of a chlorohydrin ether isomer different in alcohol added position and a 2-mole adduct of epichlorohydrin (hereinafter called “organochlorine compounds”, for simplicity) was not greater than 100 ppm. After completion of the reaction was dehydrated at 120° C. under reduced pressure (6.67 kPa) followed by purification by distillation under reduced pressure (13 to 26 Pa, 160 to 170° C.)

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

Procedure: Isopropylideneglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of tolune was added dropwise to a solution of powdered KOH (22.4 g., 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromododecane (50 g, 0.20 mol) in 40 mL of tolune was then added dropwise, and the solution was refluxed for 10 hours. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution was refluxed for 16 hours. After cooling, ice-water (150 mL) was added, and the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol, 71%) of a white solid. The resulting mixture was refluxed for 4 hours the solution was refluxed for 10 hours After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution was refluxed for 16 hours After cooling ice-water (150 mL) was added the layers were separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Procedure: Isopropylidineglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powdered KOH (22.4 g, 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromodecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 hours. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution was refluxed for 16 hours. After cooling, ice water (150 mL) was added, and the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol), 71% of a white solid. The resulting mixture was refluxed for 4 hours the solution was refluxed for 10 hours After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution was refluxed for 16 hours After cooling ice water (150 mL) was added the layers were separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Procedure: Isopropylidineglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powdered KOH (22.4 g, 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromodecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 hours. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution was refluxed for 16 hours. After cooling, ice water (150 mL) was added, and the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol), 71% of a white solid. The resulting mixture was refluxed for 4 hours the solution was refluxed for 10 hours After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution was refluxed for 16 hours After cooling ice water (150 mL) was added the layers were separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH

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

Procedure: Isopropylidineglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powdered KOH (22.4 g, 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromodecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 hours. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution was refluxed for 16 hours. After cooling, ice water (150 mL) was added, and the layers were separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol), 71% of a white solid. The resulting mixture was refluxed for 4 hours the solution was refluxed for 10 hours After cooling extracted with diethyl ether (3×100 mL) The ether layers were dried over magnesium sulfate the solvent was removed in vacuo The residue was dissolved in 60 mL of diethyl ether Concentrated HCl (60 mL) was added the solution was refluxed for 16 hours After cooling ice water (150 mL) was added the layers were separated The aqueous layer was extracted with diethyl ether (2×75 mL) The combined organic fractions were then dried over sodium sulfate filtered concentrated in vacuo The solid residue was recrystallized from MeOH