[3-methyl-3-(4-methylpent-3-enyl)oxiran-2-yl]methanol

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

Procedure: The hydroperoxide resulting from nerol can be reduced to the corresponding hydroxyl compound and this can then be cyclized with acid catalysis to give nerol oxide.

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

Conditions: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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

Conditions: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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

Conditions: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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

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

Procedure: The hydroperoxide resulting from nerol can be reduced to the corresponding hydroxyl compound and this can then be cyclized with acid catalysis to give nerol oxide.

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

Procedure: The hydroperoxide resulting from nerol can be reduced to the corresponding hydroxyl compound and this can then be cyclized with acid catalysis to give nerol oxide.

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

Procedure: Ohloff prepared the intermediate 3,7-dimethyl-octa-2,5-dien-1,7-diol from nerol by its photosensitized air oxidation followed by reduction and cyclisation with an acid to obtain racemic nerol oxide [G. Ohloff, K. H. Schulte-Elite & B. Willhalm Helv. Chim. Acta. 47, 602, 1964]. In another publication nerol was first subjected to epoxidation at C6–C7 double bond and the epoxy derivative so obtained was heated in dimethyl amine at 150° to give 3,7-dimethyl-6-dimethyl amino-2-octen-1,7-diol which on oxidation with hydrogen peroxide and pyrolysis at 180° C. gave a diol intermediate that on acid catalysed cyclisation led to the formation of nerol oxide [G. Ohloff & B. Lienhard Helv. Chim. Acta. 48, 182, 1965].

Conditions: temp:83.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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