4-ethylcyclohexan-1-ol

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

Procedure: A solution of 1-chloroethyl chloroformate (5.46 g) in dry dichloromethane (20 ml) was added dropwise, under nitrogen at 0°, to a stirred solution of 4-ethylcyclohexanol (5 g) in dry dichloromethane (20 ml) in presence of 3A molecular sieves. A solution of pyridine (3 g) in dry dichloromethane (20 ml) was added dropwise to the reaction mixture during 20 min at 0° the mixture was then warmed to 20°, stirred for 20 hours, washed with brine (2×50 ml) and dried. The solvent was removed under vacuum and the residue was distilled to give the title compound as a colourless oil (7.9 g; b.p. 130°/5.2 mbar; t.l.c. cyclohexane/ethyl acetate 9/1 Rf=0.88; IR (CDCl3), Vmax (cm-1): 1757 (C=O); 1H-NMR (300 MHz, CDCl3): 6.43 (q), 6.42 (q), 4.93 (bs), 4.59 (tt), 2.14-2.01 (bs), 2.00-1.88 (bs), 1.88-1.78 (m), 1.83 (d), 1.82 (d), 1.60-1.50 (m), 1.50-1.32 (m), 1.30-1.15 (m), 1.28-1.18 (m) 1.05-0.95 (m), 0.95-0.85 (m). was then warmed to 20° washed with brine (2×50 ml) dried The solvent was removed under vacuum the residue was distilled

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

Procedure: A solution of 1-chloroethyl chloroformate (5.46 g) in dry dichloromethane (20 ml) was added dropwise, under nitrogen at 0°, to a stirred solution of 4-ethylcyclohexanol (5 g) in dry dichloromethane (20 ml) in presence of 3A molecular sieves. A solution of pyridine (3 g) in dry dichloromethane (20 ml) was added dropwise to the reaction mixture during 20 min at 0° the mixture was then warmed to 20°, stirred for 20 hours, washed with brine (2×50 ml) and dried. The solvent was removed under vacuum and the residue was distilled to give the title compound as a colourless oil (7.9 g; b.p. 130°/5.2 mbar; t.l.c. cyclohexane/ethyl acetate 9/1 Rf=0.88; IR (CDCl3), Vmax (cm-1): 1757 (C=O); 1H-NMR (300 MHz, CDCl3): 6.43 (q), 6.42 (q), 4.93 (bs), 4.59 (tt), 2.14-2.01 (bs), 2.00-1.88 (bs), 1.88-1.78 (m), 1.83 (d), 1.82 (d), 1.60-1.50 (m), 1.50-1.32 (m), 1.30-1.15 (m), 1.28-1.18 (m) 1.05-0.95 (m), 0.95-0.85 (m). was then warmed to 20° washed with brine (2×50 ml) dried The solvent was removed under vacuum the residue was distilled

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

Procedure: In a four necked flask (2 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, resorcinol (72 g, 0.65 mol), 4-ethylcyclohexanol (92 g, 0.72 mol) and triphenylphosphine (185 g, 0.70 mol) were dissolved in dried tetrahydrofuran (700 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (132 g, 0.65 mol) and dried tetrahydrofuran (180 ml) was dropped for 1 hour while cooling with an iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30% hydrogen peroxide (140 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 1 L toluene, and washed three times with 500 ml water. Toluene was distilled away by evaporation, and the residue was purified by column chromatography using hexane and ethyl acetate as developing solvents, to obtain a red brown objective product (hereinafter, referred to as R-3A) (38.5 g, 27% yield, 99% GC purity). In a four necked flask (2 L) sufficiently dried equipped with a dropping funnel, Dimroth condenser tube while cooling with an iced saline solution After the reaction terminated 30% hydrogen peroxide (140 ml) was dropped through the dropping funnel for 10 minutes the reaction solution was dissolved in 1 L toluene washed three times with 500 ml water Toluene was distilled away by evaporation the residue was purified by column chromatography to obtain a red brown objective product (hereinafter,

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

Procedure: A solution of 1-chloroethyl chloroformate (5.46 g) in dry dichloromethane (20 ml) was added dropwise, under nitrogen at 0°, to a stirred solution of 4-ethylcyclohexanol (5 g) in dry dichloromethane (20 ml) in presence of 3A molecular sieves. A solution of pyridine (3 g) in dry dichloromethane (20 ml) was added dropwise to the reaction mixture during 20 min at 0° the mixture was then warmed to 20°, stirred for 20 hours, washed with brine (2×50 ml) and dried. The solvent was removed under vacuum and the residue was distilled to give the title compound as a colourless oil (7.9 g; b.p. 130°/5.2 mbar; t.l.c. cyclohexane/ethyl acetate 9/1 Rf=0.88; IR (CDCl3), Vmax (cm-1): 1757 (C=O); 1H-NMR (300 MHz, CDCl3): 6.43 (q), 6.42 (q), 4.93 (bs), 4.59 (tt), 2.14-2.01 (bs), 2.00-1.88 (bs), 1.88-1.78 (m), 1.83 (d), 1.82 (d), 1.60-1.50 (m), 1.50-1.32 (m), 1.30-1.15 (m), 1.28-1.18 (m) 1.05-0.95 (m), 0.95-0.85 (m). was then warmed to 20° washed with brine (2×50 ml) dried The solvent was removed under vacuum the residue was distilled

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

Procedure: In a four necked flask (2 L) sufficiently dried, substituted with nitrogen, and equipped with a dropping funnel, Dimroth condenser tube, thermometer and stirring blade, resorcinol (72 g, 0.65 mol), 4-ethylcyclohexanol (92 g, 0.72 mol) and triphenylphosphine (185 g, 0.70 mol) were dissolved in dried tetrahydrofuran (700 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (132 g, 0.65 mol) and dried tetrahydrofuran (180 ml) was dropped for 1 hour while cooling with an iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30% hydrogen peroxide (140 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 1 L toluene, and washed three times with 500 ml water. Toluene was distilled away by evaporation, and the residue was purified by column chromatography using hexane and ethyl acetate as developing solvents, to obtain a red brown objective product (hereinafter, referred to as R-3A) (38.5 g, 27% yield, 99% GC purity). In a four necked flask (2 L) sufficiently dried equipped with a dropping funnel, Dimroth condenser tube while cooling with an iced saline solution After the reaction terminated 30% hydrogen peroxide (140 ml) was dropped through the dropping funnel for 10 minutes the reaction solution was dissolved in 1 L toluene washed three times with 500 ml water Toluene was distilled away by evaporation the residue was purified by column chromatography to obtain a red brown objective product (hereinafter,