13-methyltetradecanal

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

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

Procedure: A suspended solution of activated zinc (118 mg), a small crystal of iodine, and tetrahydrofuran (3 ml) was stirred under refluxing. To the mixture was added a solution of tert-butyl bromoacetate (312 mg) and 13-methyltetradecanal (226 mg) in tetrahydrofuran (3 ml), and the reactants were stirred under refluxing for 1 hour. Anhydrous conditions were maintained throughout this experiment. The cooled solution was poured into 0.1N hydrochloric acid (5.6 ml) and the resultant solution was adjusted to pH 2.0 with 2N hydrochloric acid. The excess of zinc was filtered off and the crude products were extracted with ethyl acetate. The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution and brine, and then dried over magnesium sulfate. The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) and eluted with a mixture of cyclohexane and ethyl acetate (19:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was dried by high vacuum pump to afford an oil of tert-butyl 3-hydroxy-15-methylhexadecanoate (180 mg). under refluxing under refluxing for 1 hour Anhydrous conditions were maintained throughout this experiment The excess of zinc was filtered off the crude products were extracted with ethyl acetate The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution and brine dried over magnesium sulfate The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) eluted with a mixture of cyclohexane and ethyl acetate (19:1) The fractions containing the object compound concentrated under reduced pressure The residue was dried by high vacuum pump

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

Procedure: A suspended solution of activated zinc (118 mg), a small crystal of iodine, and tetrahydrofuran (3 ml) was stirred under refluxing. To the mixture was added a solution of tert-butyl bromoacetate (312 mg) and 13-methyltetradecanal (226 mg) in tetrahydrofuran (3 ml), and the reactants were stirred under refluxing for 1 hour. Anhydrous conditions were maintained throughout this experiment. The cooled solution was poured into 0.1N hydrochloric acid (5.6 ml) and the resultant solution was adjusted to pH 2.0 with 2N hydrochloric acid. The excess of zinc was filtered off and the crude products were extracted with ethyl acetate. The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution and brine, and then dried over magnesium sulfate. The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) and eluted with a mixture of cyclohexane and ethyl acetate (19:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was dried by high vacuum pump to afford an oil of tert-butyl 3-hydroxy-15-methylhexadecanoate (180 mg). under refluxing under refluxing for 1 hour Anhydrous conditions were maintained throughout this experiment The excess of zinc was filtered off the crude products were extracted with ethyl acetate The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution and brine dried over magnesium sulfate The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) eluted with a mixture of cyclohexane and ethyl acetate (19:1) The fractions containing the object compound concentrated under reduced pressure The residue was dried by high vacuum pump

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

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

Procedure: 13-methyl-tetradecanaldehyde (56.5 g, 0.25 mole), malonic acid (26.5 g, 0.51 mole), and pyridine (30.8 ml, 0.374 mole) were added to a flask and refluxed with heating for 3 hours. After cooling down 30% sulfuic acid was added and the reaction mixture was stirred for 3 hours under ice bath and then extracted by diethyl ether. Diethyl ether was removed by evaporation and product was subject to vacuum fractional distillation and 170–172° C./1.0 mmHg fraction was collected as 15-methyl-2-hexadecenoic acid (50.9 g, yield rate 76%). refluxed with heating for 3 hours was added extracted by diethyl ether Diethyl ether was removed by evaporation and product was subject to vacuum fractional distillation and 170–172° C./1.0 mmHg fraction was collected as 15-methyl-2-hexadecenoic acid (50.9 g, yield rate 76%)

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

Procedure: 13-methyl-tetradecanaldehyde (56.5 g, 0.25 mole), malonic acid (26.5 g, 0.51 mole), and pyridine (30.8 ml, 0.374 mole) were added to a flask and refluxed with heating for 3 hours. After cooling down 30% sulfuic acid was added and the reaction mixture was stirred for 3 hours under ice bath and then extracted by diethyl ether. Diethyl ether was removed by evaporation and product was subject to vacuum fractional distillation and 170–172° C./1.0 mmHg fraction was collected as 15-methyl-2-hexadecenoic acid (50.9 g, yield rate 76%). refluxed with heating for 3 hours was added extracted by diethyl ether Diethyl ether was removed by evaporation and product was subject to vacuum fractional distillation and 170–172° C./1.0 mmHg fraction was collected as 15-methyl-2-hexadecenoic acid (50.9 g, yield rate 76%)

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

Procedure: Chloro-chromic pyridine (161.6 g, 0.75 mole) and 450 ml dichloromethane were added to a flask. With stirring, 150 ml dichloromethane solution of 13-methyl-1-tetradecanol (114 g, 0.50 mole) was slowly added to the flask and stirring continued for 1.5 hours at room temperature. Let the mixture stand and separate into two phases. Decant upper phase and wash the remainder with 100 ml diethyl ether. Combine all liquid and wash sequentially with saturated NaCl, 10% HCl, and saturated NaCl solution with 5% NaHCO3. Desiccate with anhydrous CaCl2 and remove solvent by evaporation to yield 13-methyl-tetradecanaldehyde (57.6 g, yield rate 51%). stirring separate into two phases Decant upper phase wash the remainder with 100 ml diethyl ether Combine all liquid and wash sequentially with saturated NaCl, 10% HCl, and saturated NaCl solution with 5% NaHCO3 Desiccate with anhydrous CaCl2 and remove solvent by evaporation

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

Procedure: Activated zinc (118 mg), a small crystal of iodine, and tetrahydrofuran (3 ml) were stirred and heated under reflux. To the mixture was added a solution of tert-butyl bromoacetate (312 mg) and 13-methyltetradecanal (226 mg) in tetrahydrofuran (3 ml), and the reactants were stirred and heated under reflux for 1 hour. Anhydrous conditions were maintained throughout the experiment. The cooled solution was poured into 0.1 N hydrochloric acid (5.6 ml) and the pH was adjusted to 2.0 with 2 N hydrochloric acid. The excess of zinc was filtered off and the crude products were extracted with ethyl acetate. The ethyl acetate solution was washed with aqueous sodium hydrogen carbonate and brine, and then dried over magnesium sulfate. The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) and eluted with a mixture of cyclohexane and ethyl acetate (19:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was dried by high vacuum pump to afford an oil of tert-butyl 3-hydroxy-15-methylhexadecanoate (180 mg). heated under reflux heated under reflux for 1 hour Anhydrous conditions were maintained throughout the experiment The excess of zinc was filtered off the crude products were extracted with ethyl acetate The ethyl acetate solution was washed with aqueous sodium hydrogen carbonate and brine dried over magnesium sulfate The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) eluted with a mixture of cyclohexane and ethyl acetate (19:1) The fractions containing the object compound concentrated under reduced pressure The residue was dried by high vacuum pump

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

Procedure: A suspended solution of activated zinc (118 mg), a small crystal of iodine, and tetrahydrofuran (3 ml) was stirred under refluxing. To the mixture was added a solution of tert-butyl bromoacetate (312 mg) and 13-methyltetradecanal (226 mg) in tetrahydrofuran (3 ml), and the reactants were stirred under refluxing for 1 hour. Anhydrous conditions were maintained throughout this experiment. The cooled solution was poured into 0.1N hydrochloric acid (5.6 ml) and the resultant solution was adjusted to pH 2.0 with 2N hydrochloric acid. The excess of zinc was filtered off and the crude products were extracted with ethyl acetate. The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution and brine, and then dried over magnesium sulfate. The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) and eluted with a mixture of cyclohexane and ethyl acetate (19:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was dried by high vacuum pump to afford an oil of tert-butyl 3-hydroxy-15-methylhexadecanoate (180 mg). under refluxing under refluxing for 1 hour Anhydrous conditions were maintained throughout this experiment The excess of zinc was filtered off the crude products were extracted with ethyl acetate The ethyl acetate layer was washed with aqueous sodium hydrogen carbonate solution and brine dried over magnesium sulfate The ethyl acetate was evaporated off under reduced pressure to give the crude ester, which was purified by column chromatography on silica gel (Merck) eluted with a mixture of cyclohexane and ethyl acetate (19:1) The fractions containing the object compound concentrated under reduced pressure The residue was dried by high vacuum pump