heptanenitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml. flask, equipped with magnetic stirrer, heating mantle, thermometer, condensor and calcium sulfate drying tube, was charged 1.12 g. of 4-methyl cyclohexanone (0.01 M), 11.1 g. of heptanonitrile, and 0.66 g. of 85% KOH. The mixture was heated to reflux with stirring at about 83° C. for a total of 32 hours. After cooling, 30 ml. of hexane was added and the mixture washed seven times with 30 ml. of H2O, each washing being back-extracted twice with 30 ml. portions of hexane. The combined organic phase and hexane extracts were dried over anhydrous sodium sulfate and the solvent removed by rotary evaporation at about 15 mm. Hg to give 6.3 g. of crude oil. Gas chromatographic analysis (6' × 1/4" stainless steel column packed with 20% SE30 on chromasorb W, programmed at 135° to 220° C., 4°/minute, He flow ~60 ml./minute) showed two product peaks at RF 19.0 and 20.2 minutes, which were 6.9% in ratio to heptanonitrile. An IR spectrum of the product peaks, trapped as a group from the gas chromatograph, showed a nitrile band at 4.5 microns and an olefinic band at 6.25 microns. The product was evaluated by perfumers as having a jasminic nitrile type odor with a strong, nerol oxide note. flask, equipped with magnetic stirrer heating mantle The mixture was heated to reflux After cooling the mixture washed seven times with 30 ml of H2O, each washing being back-extracted twice with 30 ml The combined organic phase and hexane extracts were dried over anhydrous sodium sulfate the solvent removed by rotary evaporation at about 15 mm. Hg to give 6.3 g programmed at 135° to 220° C. at RF 19.0 and 20.2 minutes, which

反応条件: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml. flask, equipped with magnetic stirrer, heating mantle, thermometer, condensor and calcium sulfate drying tube, was charged 1.12 g. of 4-methyl cyclohexanone (0.01 M), 11.1 g. of heptanonitrile, and 0.66 g. of 85% KOH. The mixture was heated to reflux with stirring at about 83° C. for a total of 32 hours. After cooling, 30 ml. of hexane was added and the mixture washed seven times with 30 ml. of H2O, each washing being back-extracted twice with 30 ml. portions of hexane. The combined organic phase and hexane extracts were dried over anhydrous sodium sulfate and the solvent removed by rotary evaporation at about 15 mm. Hg to give 6.3 g. of crude oil. Gas chromatographic analysis (6' × 1/4" stainless steel column packed with 20% SE30 on chromasorb W, programmed at 135° to 220° C., 4°/minute, He flow ~60 ml./minute) showed two product peaks at RF 19.0 and 20.2 minutes, which were 6.9% in ratio to heptanonitrile. An IR spectrum of the product peaks, trapped as a group from the gas chromatograph, showed a nitrile band at 4.5 microns and an olefinic band at 6.25 microns. The product was evaluated by perfumers as having a jasminic nitrile type odor with a strong, nerol oxide note. flask, equipped with magnetic stirrer heating mantle The mixture was heated to reflux After cooling the mixture washed seven times with 30 ml of H2O, each washing being back-extracted twice with 30 ml The combined organic phase and hexane extracts were dried over anhydrous sodium sulfate the solvent removed by rotary evaporation at about 15 mm. Hg to give 6.3 g programmed at 135° to 220° C. at RF 19.0 and 20.2 minutes, which

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml. flask, equipped with magnetic stirrer, heating mantle, condensor, calcium sulfate drying tube, constant temperature controller and thermometer, was charged 0.98 g. of cyclohexanone (0.01 M), 11.1 g. of heptanonitrile (0.10 M) and 0.66 g. of 85% potassium hydroxide flakes. The mixture was heated cooled, 30 ml. of hexane was added, and the mixture washed six times with 30 ml. portions of water and once with saturated brine. The washes were each in succession, cross-extracted with two 15 ml. portions of hexane. The combined organic and hexane phases were dried over anhydrous sodium sulfate and solvent evaporated on a rotary evaporator at ~30 mm. Hg to give 6.7 g. of oil. Gas chromatographic analysis (6' × 1/4" column, 20% Carbowax 20 m. on Chromasorb W, programmed 135° C. to 220° C. at 4°/minute, He flow ~60 ml./minute) showed product nitrile peaks at 17.8 minutes (10.3%) and 20.1 minutes (4.1%) with heptanonitrile at 4.3 minutes (85.5%). The product peaks which eluted together at 17.6 minutes on a 20% SE30 column (6' × 1/4") under the same operating parameters were trapped out for odor evaluation. An IR spectrum on the trapping of combined isomers showed a nitrile band at 4.5 microns and an olefin band at 6.27 microns. The product was described by perfumers as having an interesting, fruity, floral, salicylate quality. flask, equipped with magnetic stirrer was charged 0.98 g The mixture was heated cooled the mixture washed six times with 30 ml cross-extracted with two 15 ml The combined organic and hexane phases were dried over anhydrous sodium sulfate and solvent evaporated on a rotary evaporator at ~30 mm. Hg to give 6.7 g programmed 135° C. to 220° C. at 4°/minute, He at 17.8 minutes (10.3%) and 20.1 minutes (4.1%) at 4.3 minutes The product peaks which eluted together at 17.6 minutes on a 20% SE30 column (6' × 1/4") under the same operating parameters

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml. flask, equipped with magnetic stirrer, heating mantle, condensor, calcium sulfate drying tube, constant temperature controller and thermometer, was charged 0.98 g. of cyclohexanone (0.01 M), 11.1 g. of heptanonitrile (0.10 M) and 0.66 g. of 85% potassium hydroxide flakes. The mixture was heated cooled, 30 ml. of hexane was added, and the mixture washed six times with 30 ml. portions of water and once with saturated brine. The washes were each in succession, cross-extracted with two 15 ml. portions of hexane. The combined organic and hexane phases were dried over anhydrous sodium sulfate and solvent evaporated on a rotary evaporator at ~30 mm. Hg to give 6.7 g. of oil. Gas chromatographic analysis (6' × 1/4" column, 20% Carbowax 20 m. on Chromasorb W, programmed 135° C. to 220° C. at 4°/minute, He flow ~60 ml./minute) showed product nitrile peaks at 17.8 minutes (10.3%) and 20.1 minutes (4.1%) with heptanonitrile at 4.3 minutes (85.5%). The product peaks which eluted together at 17.6 minutes on a 20% SE30 column (6' × 1/4") under the same operating parameters were trapped out for odor evaluation. An IR spectrum on the trapping of combined isomers showed a nitrile band at 4.5 microns and an olefin band at 6.27 microns. The product was described by perfumers as having an interesting, fruity, floral, salicylate quality. flask, equipped with magnetic stirrer was charged 0.98 g The mixture was heated cooled the mixture washed six times with 30 ml cross-extracted with two 15 ml The combined organic and hexane phases were dried over anhydrous sodium sulfate and solvent evaporated on a rotary evaporator at ~30 mm. Hg to give 6.7 g programmed 135° C. to 220° C. at 4°/minute, He at 17.8 minutes (10.3%) and 20.1 minutes (4.1%) at 4.3 minutes The product peaks which eluted together at 17.6 minutes on a 20% SE30 column (6' × 1/4") under the same operating parameters

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of potassium tert-butoxide (18.9 g) in a mixed solvent system of tetrahydrofuran (150 ml) and toluene (100 ml) was heated to 75° . A solution of heptanonitrile (11.2 g) and ethyl formate (24 ml) in toluene (50 ml) was then added dropwise to the warm tert-butoxide solution. The reaction was stirred for 5 hours at 75° then cooled with an ice bath. Ether was added to the mixture and then water. The layers were separated. The aqueous phase was washed once with ether then acidified to a pH of about 3 with aqueous hydrochloric acid (6N). The aqueous phase was saturated with sodium chloride then extracted twice with ether. The combined ether extracts were washed with brine, dried (MgSO4) and concentrated to leave the title product as a yellow oil (10.7 g, 77%). then cooled with an ice bath The layers were separated The aqueous phase was washed once with ether then extracted twice with ether The combined ether extracts were washed with brine dried (MgSO4) concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of potassium tert-butoxide (18.9 g) in a mixed solvent system of tetrahydrofuran (150 ml) and toluene (100 ml) was heated to 75° . A solution of heptanonitrile (11.2 g) and ethyl formate (24 ml) in toluene (50 ml) was then added dropwise to the warm tert-butoxide solution. The reaction was stirred for 5 hours at 75° then cooled with an ice bath. Ether was added to the mixture and then water. The layers were separated. The aqueous phase was washed once with ether then acidified to a pH of about 3 with aqueous hydrochloric acid (6N). The aqueous phase was saturated with sodium chloride then extracted twice with ether. The combined ether extracts were washed with brine, dried (MgSO4) and concentrated to leave the title product as a yellow oil (10.7 g, 77%). then cooled with an ice bath The layers were separated The aqueous phase was washed once with ether then extracted twice with ether The combined ether extracts were washed with brine dried (MgSO4) concentrated

反応条件: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml. flask, equipped with magnetic stirrer, heating mantle, thermometer, condensor and calcium sulfate drying tube, was charged 1.12 g. of 4-methyl cyclohexanone (0.01 M), 11.1 g. of heptanonitrile, and 0.66 g. of 85% KOH. The mixture was heated to reflux with stirring at about 83° C. for a total of 32 hours. After cooling, 30 ml. of hexane was added and the mixture washed seven times with 30 ml. of H2O, each washing being back-extracted twice with 30 ml. portions of hexane. The combined organic phase and hexane extracts were dried over anhydrous sodium sulfate and the solvent removed by rotary evaporation at about 15 mm. Hg to give 6.3 g. of crude oil. Gas chromatographic analysis (6' × 1/4" stainless steel column packed with 20% SE30 on chromasorb W, programmed at 135° to 220° C., 4°/minute, He flow ~60 ml./minute) showed two product peaks at RF 19.0 and 20.2 minutes, which were 6.9% in ratio to heptanonitrile. An IR spectrum of the product peaks, trapped as a group from the gas chromatograph, showed a nitrile band at 4.5 microns and an olefinic band at 6.25 microns. The product was evaluated by perfumers as having a jasminic nitrile type odor with a strong, nerol oxide note. flask, equipped with magnetic stirrer heating mantle The mixture was heated to reflux After cooling the mixture washed seven times with 30 ml of H2O, each washing being back-extracted twice with 30 ml The combined organic phase and hexane extracts were dried over anhydrous sodium sulfate the solvent removed by rotary evaporation at about 15 mm. Hg to give 6.3 g programmed at 135° to 220° C. at RF 19.0 and 20.2 minutes, which

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 25 ml. flask, equipped with magnetic stirrer, heating mantle, condensor, calcium sulfate drying tube, constant temperature controller and thermometer, was charged 0.98 g. of cyclohexanone (0.01 M), 11.1 g. of heptanonitrile (0.10 M) and 0.66 g. of 85% potassium hydroxide flakes. The mixture was heated cooled, 30 ml. of hexane was added, and the mixture washed six times with 30 ml. portions of water and once with saturated brine. The washes were each in succession, cross-extracted with two 15 ml. portions of hexane. The combined organic and hexane phases were dried over anhydrous sodium sulfate and solvent evaporated on a rotary evaporator at ~30 mm. Hg to give 6.7 g. of oil. Gas chromatographic analysis (6' × 1/4" column, 20% Carbowax 20 m. on Chromasorb W, programmed 135° C. to 220° C. at 4°/minute, He flow ~60 ml./minute) showed product nitrile peaks at 17.8 minutes (10.3%) and 20.1 minutes (4.1%) with heptanonitrile at 4.3 minutes (85.5%). The product peaks which eluted together at 17.6 minutes on a 20% SE30 column (6' × 1/4") under the same operating parameters were trapped out for odor evaluation. An IR spectrum on the trapping of combined isomers showed a nitrile band at 4.5 microns and an olefin band at 6.27 microns. The product was described by perfumers as having an interesting, fruity, floral, salicylate quality. flask, equipped with magnetic stirrer was charged 0.98 g The mixture was heated cooled the mixture washed six times with 30 ml cross-extracted with two 15 ml The combined organic and hexane phases were dried over anhydrous sodium sulfate and solvent evaporated on a rotary evaporator at ~30 mm. Hg to give 6.7 g programmed 135° C. to 220° C. at 4°/minute, He at 17.8 minutes (10.3%) and 20.1 minutes (4.1%) at 4.3 minutes The product peaks which eluted together at 17.6 minutes on a 20% SE30 column (6' × 1/4") under the same operating parameters