5-hexyloxolan-2-one

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

Procedure: 1-undecen-5-ol (8.5 g., 0.005 mol) dissolved in methanol (100 mL) was ozonized while being cooled in a dry ice-isopropanol bath. Upon completion of ozonolysis, excess ozone was expelled with a stream of oxygen, the ozonide was then treated with 50% H2O2 (10 ml) and 10% sodium hydroxide (40 ml) at room temperature for 20 hour. Acidification and extraction with methylene chloride yielded a product which was distilled to give 4-decanolide (5.5 g., 65% yield; b.p. 140°-145°/10 torr). while being cooled in a dry ice-isopropanol bath Acidification and extraction with methylene chloride yielded a product which was distilled

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

Procedure: 1-undecen-5-ol (8.5 g., 0.005 mol) dissolved in methanol (100 mL) was ozonized while being cooled in a dry ice-isopropanol bath. Upon completion of ozonolysis, excess ozone was expelled with a stream of oxygen, the ozonide was then treated with 50% H2O2 (10 ml) and 10% sodium hydroxide (40 ml) at room temperature for 20 hour. Acidification and extraction with methylene chloride yielded a product which was distilled to give 4-decanolide (5.5 g., 65% yield; b.p. 140°-145°/10 torr). while being cooled in a dry ice-isopropanol bath Acidification and extraction with methylene chloride yielded a product which was distilled

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

Procedure: Octene-1 in an amount of 2.2 g. and 23.6 g. of ceric ammonium nitrate, Ce(NH4)2 (NO3)6, were refluxed under nitrogen in 200 ml. glacial acetic acid containing 60 g. potassium acetate for less than 0.5 hour, there being obtained a 48% yield of gamma-n-hexyl-butyrolactone.

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

Procedure: Octene-1 in an amount of 2.24 g. and 5.1 g. of Mn2O3 (comprising two equivalents of Mn+3 based on titration value) were refluxed under nitrogen in 200 ml. glacial acetic acid containing 60 g. potassium acetate. After a period of less than two hours, gamma-n-hexyl-butyrolactone was obtained in a yield of 61%. After a period of less than two hours

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

Procedure: Octene-1 in an amount of 3.37 g. and 4.8 g. of freshly prepared MnO2.4H2O were mixed with and heated under nitrogen in 300 ml. glacial acetic acid containing 90 g. potassium acetate. After a reaction time of less than two hours, gamma-n-hexyl-butyrolactone was obtained in 74% yield. heated under nitrogen in 300 ml

Conditions: temp:138.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: About 1.69 g. (0.015 mole) octene-1 and 8.1 g. (0.03 mole) manganic acetate were added to 73 ml. glacial acetic acid and the mixture sealed in a tube. No potassium acetate was used. The tube was placed in an oil bath maintained at 138° C., and after 4 hours the characteristic dark brown color due to manganic ion disappeared. The reaction was stopped and the reaction mixture worked up by extracting with ether and water. Gamma-n-hexyl-butyrolactone was obtained in a yield of 2.0 g., comprising 78% of theory. The tube was placed in an oil bath by extracting with ether and water

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

Procedure: Octene-1 in an amount of 2.2 grams and 23.6 grams of ceric acetate were refluxed under nitrogen in 200 milliliters of glacial acetic acid containing 60 grams of potassium acetate for less than 0.4 hour, there being obtained a 31% yield of gamma-n-hexyl butyrolactone.

Conditions: temp:165.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To an autoclave (a volume of 1 L) was charged 349 g (3.0 mol) of n-heptanol and 0.06 g (0.27 mmol) of zinc bromide. The mixture was heated and stirred at 165° C. Into the mixture in this state was injected a mixed liquor of 57 g (0.66 mol) of methyl acrylate and 9.9 g (0.068 mol) of di-t-butylperoxide over 6 hours. The resulting mixture was stirred at the temperature for further 1 hour. Subsequently, unreacted n-heptanol was distilled off followed by vacuum distillation, yielding γ-decalactone. Gas chromatographic analysis showed that the yield of γ-decalactone was 69%. The resulting γ-decalactone was plastic-like in odor and acidulous, which indicated an inferior aroma. The mixture was heated over 6 hours The resulting mixture was stirred at the temperature for further 1 hour Subsequently, unreacted n-heptanol was distilled off followed by vacuum distillation

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 200 ml of 99.5% ethanol, was dissolved 24.2 g (0.10 mol) of isobutyl 4-oxodecanoate. Thereto was added 4.2 g (0.11 mol) of sodium borohydride in small quantities, and then the mixture was stirred for 10 minutes at 25° C. The solution was poured into 1 L of water, and 1 L of ethyl acetate was further added thereto followed by stirring to thereby extract the product into the ethyl acetate phase. Ethyl acetate was distilled off followed by vacuum distillation, yielding γ-decalactone (a compound in which R61 represents an n-pentyl group in the above formula (39)). Gas chromatographic analysis showed that the yield of γ-decalactone relative to isobutyl 4-oxodecanoate was 93%. In the resulting γ-decalactone, a plastic-like flavor or acid taste was not observed at all, but it had a good peach-like aroma. was further added by stirring to thereby extract the product into the ethyl acetate phase Ethyl acetate was distilled off followed by vacuum distillation

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 200 ml of 99.5% ethanol, was dissolved 24.2 g (0.10 mol) of isobutyl 4-oxodecanoate. Thereto was added 4.2 g (0.11 mol) of sodium borohydride in small quantities, and then the mixture was stirred for 10 minutes at 25° C. The solution was poured into 1 L of water, and 1 L of ethyl acetate was further added thereto followed by stirring to thereby extract the product into the ethyl acetate phase. Ethyl acetate was distilled off followed by vacuum distillation, yielding γ-decalactone (a compound in which R61 represents an n-pentyl group in the above formula (39)). Gas chromatographic analysis showed that the yield of γ-decalactone relative to isobutyl 4-oxodecanoate was 93%. In the resulting γ-decalactone, a plastic-like flavor or acid taste was not observed at all, but it had a good peach-like aroma. was further added by stirring to thereby extract the product into the ethyl acetate phase Ethyl acetate was distilled off followed by vacuum distillation

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

Procedure: Octene-1 in an amount of 2.2 g. and 23.6 g. of ceric ammonium nitrate, Ce(NH4)2 (NO3)6, were refluxed under nitrogen in 200 ml. glacial acetic acid containing 60 g. potassium acetate for less than 0.5 hour, there being obtained a 48% yield of gamma-n-hexyl-butyrolactone.

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

Procedure: Octene-1 in an amount of 2.24 g. and 5.1 g. of Mn2O3 (comprising two equivalents of Mn+3 based on titration value) were refluxed under nitrogen in 200 ml. glacial acetic acid containing 60 g. potassium acetate. After a period of less than two hours, gamma-n-hexyl-butyrolactone was obtained in a yield of 61%. After a period of less than two hours