1,20-EICOSANEDIOL

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

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

Procedure: Hydrogenation of 10-eicosene-1,20-diol: Two hundred fifty grams of the 10-eicosene-1,20-diol were placed in a twelve liter flask outfitted with a heating mantle, mechanical stirrer, condenser, and nitrogen inlet. Three liters of xylenes were added. Two equivalents each tributylamine and toluenesulfonhydrazide were added. Stirring and nitrogen flow were initiated and the solution slowly heated until the reaction was at reflux. The reaction was refluxed overnight, and then cooled to room temperature. The product, 1,20-eicosanediol, precipitated from solution and was filtered, washing with methanol. The crude product was recrystallized once from methanol, yielding white crystals with a melting point of about 101° C. The product was 99% pure by gas chromatography. IR(KBr): 3419, 3357, 2919, 2848, 1469, 1355, 1321, 1124, 1055, 1034, 999, 969, 722, 610, 502 cm−1; 1H NMR(300 MHz, toluene-d8, elevated temperature): * 3.3 (t, 4H), 1.3 (bd, 36H), 0.5 (m, 2H). the solution slowly heated until the reaction at reflux The reaction was refluxed overnight The product, 1,20-eicosanediol, precipitated from solution was filtered washing with methanol The crude product was recrystallized once from methanol yielding white crystals with a melting point of about 101° C

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

Procedure: Hydrogenation of 10-eicosene-1,20-diol: Two hundred fifty grams of the 10-eicosene-1,20-diol were placed in a twelve liter flask outfitted with a heating mantle, mechanical stirrer, condenser, and nitrogen inlet. Three liters of xylenes were added. Two equivalents each tributylamine and toluenesulfonhydrazide were added. Stirring and nitrogen flow were initiated and the solution slowly heated until the reaction was at reflux. The reaction was refluxed overnight, and then cooled to room temperature. The product, 1,20-eicosanediol, precipitated from solution and was filtered, washing with methanol. The crude product was recrystallized once from methanol, yielding white crystals with a melting point of about 101° C. The product was 99% pure by gas chromatography. IR(KBr): 3419, 3357, 2919, 2848, 1469, 1355, 1321, 1124, 1055, 1034, 999, 969, 722, 610, 502 cm−1; 1H NMR(300 MHz, toluene-d8, elevated temperature): * 3.3 (t, 4H), 1.3 (bd, 36H), 0.5 (m, 2H). the solution slowly heated until the reaction at reflux The reaction was refluxed overnight The product, 1,20-eicosanediol, precipitated from solution was filtered washing with methanol The crude product was recrystallized once from methanol yielding white crystals with a melting point of about 101° C

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

Procedure: 20-Bromo-icosan-1-ol was synthesized according to Uneyama et al, Tetrahedron Letters, 1991, 32(11), 1459-1462. Briefly, 400 ml petrolether were heated before 240 ml petrolether, 20.34 g icosane-1,20-diol and 280 ml HBr (48% in H2O) were added. The mixture was refluxed over night and incubated at room temperature for another day. The precipitate was then removed by filtration and dissolved in 300 ml dichloromethane. The solution was dried over Na2SO4 and filtered through silica gel. The solvent was removed and the crude product finally recrystallized from petrolether. Purity of the product was judged by 1H-NMR. were added The mixture was refluxed over night incubated at room temperature for another day The precipitate was then removed by filtration dissolved in 300 ml dichloromethane The solution was dried over Na2SO4 filtered through silica gel The solvent was removed the crude product finally recrystallized from petrolether

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

Procedure: Icosane-1,20-diol was synthesized according to Yoon et al., J. Org. Chem. 1973, 38(16), 2786-2792. Briefly, under N2 atmosphere to 25 g eicosanedioic acid 100 ml THF was added. Then 474.5 ml of borane/THF complex was added dropwise over 1.5 hours. The mixture was refluxed over night before 200 ml THF/H2O 1:1 were added dropwise. Under further stirring 100 g NaHCO3 dissolved in 250 ml H2O was added and two hours later 1000 ml H2O was added to the mixture and the precipitate was removed by filtration. At the next day and the day after next a white precipitate was removed by filtration from the mixture, dried and recrystallized from acetic acid ethyl ester. The product was characterized by thin layer chromatography and 1H-NMR. Then 474.5 ml of borane/THF complex was added dropwise over 1.5 hours were added dropwise was added to the mixture the precipitate was removed by filtration At the next day and the day after next a white precipitate was removed by filtration from the mixture dried recrystallized from acetic acid ethyl ester

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

Procedure: 20-Bromo-icosan-1-ol was synthesized according to Uneyama et al, Tetrahedron Letters, 1991, 32(11), 1459-1462. Briefly, 400 ml petrolether were heated before 240 ml petrolether, 20.34 g icosane-1,20-diol and 280 ml HBr (48% in H2O) were added. The mixture was refluxed over night and incubated at room temperature for another day. The precipitate was then removed by filtration and dissolved in 300 ml dichloromethane. The solution was dried over Na2SO4 and filtered through silica gel. The solvent was removed and the crude product finally recrystallized from petrolether. Purity of the product was judged by 1H-NMR. were added The mixture was refluxed over night incubated at room temperature for another day The precipitate was then removed by filtration dissolved in 300 ml dichloromethane The solution was dried over Na2SO4 filtered through silica gel The solvent was removed the crude product finally recrystallized from petrolether

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

Procedure: Icosane-1,20-diol was synthesized according to Yoon et al., J. Org. Chem. 1973, 38(16), 2786-2792. Briefly, under N2 atmosphere to 25 g eicosanedioic acid 100 ml THF was added. Then 474.5 ml of borane/THF complex was added dropwise over 1.5 hours. The mixture was refluxed over night before 200 ml THF/H2O 1:1 were added dropwise. Under further stirring 100 g NaHCO3 dissolved in 250 ml H2O was added and two hours later 1000 ml H2O was added to the mixture and the precipitate was removed by filtration. At the next day and the day after next a white precipitate was removed by filtration from the mixture, dried and recrystallized from acetic acid ethyl ester. The product was characterized by thin layer chromatography and 1H-NMR. Then 474.5 ml of borane/THF complex was added dropwise over 1.5 hours were added dropwise was added to the mixture the precipitate was removed by filtration At the next day and the day after next a white precipitate was removed by filtration from the mixture dried recrystallized from acetic acid ethyl ester

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

Procedure: Hydrogenation of 10-eicosene-1,20-diol: Two hundred fifty grams of the 10-eicosene-1,20-diol were placed in a twelve liter flask outfitted with a heating mantle, mechanical stirrer, condenser, and nitrogen inlet. Three liters of xylenes were added. Two equivalents each tributylamine and toluenesulfonhydrazide were added. Stirring and nitrogen flow were initiated and the solution slowly heated until the reaction was at reflux. The reaction was refluxed overnight, and then cooled to room temperature. The product, 1,20-eicosanediol, precipitated from solution and was filtered, washing with methanol. The crude product was recrystallized once from methanol, yielding white crystals with a melting point of about 101° C. The product was 99% pure by gas chromatography. IR(KBr): 3419, 3357, 2919, 2848, 1469, 1355, 1321, 1124, 1055, 1034, 999, 969, 722, 610, 502 cm−1; 1H NMR(300 MHz, toluene-d8, elevated temperature): * 3.3 (t, 4H), 1.3 (bd, 36H), 0.5 (m, 2H). the solution slowly heated until the reaction at reflux The reaction was refluxed overnight The product, 1,20-eicosanediol, precipitated from solution was filtered washing with methanol The crude product was recrystallized once from methanol yielding white crystals with a melting point of about 101° C

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

Procedure: 20-Bromo-icosan-1-ol was synthesized according to Uneyama et al, Tetrahedron Letters, 1991, 32(11), 1459-1462. Briefly, 400 ml petrolether were heated before 240 ml petrolether, 20.34 g icosane-1,20-diol and 280 ml HBr (48% in H2O) were added. The mixture was refluxed over night and incubated at room temperature for another day. The precipitate was then removed by filtration and dissolved in 300 ml dichloromethane. The solution was dried over Na2SO4 and filtered through silica gel. The solvent was removed and the crude product finally recrystallized from petrolether. Purity of the product was judged by 1H-NMR. were added The mixture was refluxed over night incubated at room temperature for another day The precipitate was then removed by filtration dissolved in 300 ml dichloromethane The solution was dried over Na2SO4 filtered through silica gel The solvent was removed the crude product finally recrystallized from petrolether

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

Procedure: Icosane-1,20-diol was synthesized according to Yoon et al., J. Org. Chem. 1973, 38(16), 2786-2792. Briefly, under N2 atmosphere to 25 g eicosanedioic acid 100 ml THF was added. Then 474.5 ml of borane/THF complex was added dropwise over 1.5 hours. The mixture was refluxed over night before 200 ml THF/H2O 1:1 were added dropwise. Under further stirring 100 g NaHCO3 dissolved in 250 ml H2O was added and two hours later 1000 ml H2O was added to the mixture and the precipitate was removed by filtration. At the next day and the day after next a white precipitate was removed by filtration from the mixture, dried and recrystallized from acetic acid ethyl ester. The product was characterized by thin layer chromatography and 1H-NMR. Then 474.5 ml of borane/THF complex was added dropwise over 1.5 hours were added dropwise was added to the mixture the precipitate was removed by filtration At the next day and the day after next a white precipitate was removed by filtration from the mixture dried recrystallized from acetic acid ethyl ester