heptane-3,5-diol

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

Procedure: To 0.03 mol 3,5-heptandiol were added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 0.075 mol benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by column chromatography to give 3,5-heptandiol dibenzoate as a colorless viscous liquid, and the yield was 92%. The reaction was heated refluxing for 4 hours cooled added 20 ml saturated saline The reaction mixture was extracted with ethyl acetate the extract was dried over anhydrous sodium sulfate filtered After removing solvent the crude was purified by column chromatography

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

Procedure: To the mixture of 2.5 g sodium borohydride, 0.05 g sodium hydroxide, and 25 ml water, was added dropwise the solution of 14.2 g 3,5-heptandione in 30 ml methanol at 0-10° C. Upon completion, the solvent was removed by reduced pressure distillation, and the residue was continuously extracted with 40 ml ethyl acetate for 15 hours. The solvent was removed to give 3,5-heptandiol as a white solid with the yield 90%, m.p. 60-65° C. IR spectrum had a strong absorption peak at 3400 cm−1, but had no absorption peak at about 1700 cm−1. Upon completion, the solvent was removed by reduced pressure distillation the residue was continuously extracted with 40 ml ethyl acetate for 15 hours The solvent was removed

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

Procedure: To 0.03 mol 3,5-heptandiol were added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 0.075 mol benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by column chromatography to give 3,5-heptandiol dibenzoate as a colorless viscous liquid, and the yield was 92%. The reaction was heated refluxing for 4 hours cooled added 20 ml saturated saline The reaction mixture was extracted with ethyl acetate the extract was dried over anhydrous sodium sulfate filtered After removing solvent the crude was purified by column chromatography

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

Procedure: To the mixture of 2.5 g sodium borohydride, 0.05 g sodium hydroxide, and 25 ml water, was added dropwise the solution of 14.2 g 3,5-heptandione in 30 ml methanol at 0-10° C. Upon completion, the solvent was removed by reduced pressure distillation, and the residue was continuously extracted with 40 ml ethyl acetate for 15 hours. The solvent was removed to give 3,5-heptandiol as a white solid with the yield 90%, m.p. 60-65° C. IR spectrum had a strong absorption peak at 3400 cm−1, but had no absorption peak at about 1700 cm−1. Upon completion, the solvent was removed by reduced pressure distillation the residue was continuously extracted with 40 ml ethyl acetate for 15 hours The solvent was removed

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

Procedure: To 0.03 mol 3,5-heptandiol were added 30 ml tetrahydrofuran and 0.09 mol pyridine, then added 0.075 mol benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by column chromatography to give 3,5-heptandiol dibenzoate as a colorless viscous liquid, and the yield was 92%. The reaction was heated refluxing for 4 hours cooled added 20 ml saturated saline The reaction mixture was extracted with ethyl acetate the extract was dried over anhydrous sodium sulfate filtered After removing solvent the crude was purified by column chromatography

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

Procedure: To the mixture of 2.5 g sodium borohydride, 0.05 g sodium hydroxide, and 25 ml water, was added dropwise the solution of 14.2 g 3,5-heptandione in 30 ml methanol at 0-10° C. Upon completion, the solvent was removed by reduced pressure distillation, and the residue was continuously extracted with 40 ml ethyl acetate for 15 hours. The solvent was removed to give 3,5-heptandiol as a white solid with the yield 90%, m.p. 60-65° C. IR spectrum had a strong absorption peak at 3400 cm−1, but had no absorption peak at about 1700 cm−1. Upon completion, the solvent was removed by reduced pressure distillation the residue was continuously extracted with 40 ml ethyl acetate for 15 hours The solvent was removed