4-methylcyclohexan-1-ol

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

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

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

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

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

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 (110 g, 1.0 mol), 4-methylcyclohexanol (114 g, 1.0 mol) and triphenylphosphine (393 g, 1.5 mol) were dissolved in dried tetrahydrofuran (500 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (269 g, 1.3 mol) and dried tetrahydrofuran (400 ml) was dropped for 1 hour while cooling with iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30% hydrogen peroxide (200 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 2 L toluene, and washed three times with 1 L 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-2A) (45.0 g, 22% yield, 97% GC purity). In a four necked flask (2 L) sufficiently dried equipped with a dropping funnel, Dimroth condenser tube while cooling with iced saline solution After the reaction terminated 30% hydrogen peroxide (200 ml) was dropped through the dropping funnel for 10 minutes the reaction solution was dissolved in 2 L toluene washed three times with 1 L 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: 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 (110 g, 1.0 mol), 4-methylcyclohexanol (114 g, 1.0 mol) and triphenylphosphine (393 g, 1.5 mol) were dissolved in dried tetrahydrofuran (500 ml) under a nitrogen gas stream, and a mixed solution of diisopropyl azodicarboxylate (269 g, 1.3 mol) and dried tetrahydrofuran (400 ml) was dropped for 1 hour while cooling with iced saline solution. Next, it was stirred at room temperature for 12 hours. After the reaction terminated, 30% hydrogen peroxide (200 ml) was dropped through the dropping funnel for 10 minutes, then the reaction solution was dissolved in 2 L toluene, and washed three times with 1 L 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-2A) (45.0 g, 22% yield, 97% GC purity). In a four necked flask (2 L) sufficiently dried equipped with a dropping funnel, Dimroth condenser tube while cooling with iced saline solution After the reaction terminated 30% hydrogen peroxide (200 ml) was dropped through the dropping funnel for 10 minutes the reaction solution was dissolved in 2 L toluene washed three times with 1 L 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:

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

Procedure: The procedure of Example 25 was repeated, except that 4-methylcyclohexanone (2 mmol) and 4-methylcyclohexanol (20 mmol) were respectively used in stead of cyclohexanone and cyclohexanol. As a result, γ-methyl-ε-caprolactone was formed in yield of 45.6% (on 4-methylcyclohexanone basis).

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 750 ml sulfonation flask equipped with thermometer, reflux condenser, N2 inlet and metering device is charged with 114.19 g (1.0 mol) of 4-methylcyclohexanol and 0.81 g of catalyst G and the reaction mixture is heated to 100° C. With efficient stirring, 98.0 ml (1.25 mol) of epichlorohydrin are added, and the reaction mixture is thereafter allowed to react for 1 h. After cooling to 50° C., 1 g of tetramethylammonium chloride is added and to the solution are then added 8 g (0.1 mol) of a 50% aqueous solution of NaOH over 5 min, followed by the addition of 42 g (1.05 mol) of pulverised NaOH in increments over 45 min and the suspension is stirred for 5 h. After addition of 200 ml of ethyl acetate, the reaction mixture is filtered, washed with 100 ml of ethyl acetate and the phases are separated. The organic phase is dried over MgSO 4, filtered, and the filtrate is freed from solvent on a rotary evaporator at a bath temperature of 60° C., giving 184.2 g (108% of theory) of colourless glycidyl ether of 4-methylcyclohexanol having the following properties: epoxy value: 4.65 eq/kg (79% of theory); total chlorine content: 5.95%; concentration of hydrolisable chlorine: 330 ppm. A 750 ml sulfonation flask equipped with thermometer reflux condenser, N2 inlet to react for 1 h After cooling to 50° C. the reaction mixture is filtered washed with 100 ml of ethyl acetate the phases are separated The organic phase is dried over MgSO 4 filtered the filtrate is freed from solvent on a rotary evaporator at a bath temperature of 60° C.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 750 ml sulfonation flask equipped with thermometer, reflux condenser, N2 inlet and metering device, 114.19 g (1.0 mol) of 4-methylcyclohexanol are added to 1.7 g of catalyst B and the reaction mixture is heated to 100° C. With efficient stirring, 98.0 ml (1.25 mol) of epichlorohydrin are added, and the reaction mixture is thereafter allowed to react for 3 h. After cooling to 50° C., 1 g of tetramethylammonium chloride is added and to the solution are then added 8 g (0.1 mol) of a 50% aqueous solution of NaOH over 5 min, followed by the addition of 42 g (1.05 mol) of pulverised NaOH in increments over 45 min and the suspension is stirred for 7 h. After addition of 200 ml of ethyl acetate, the reaction mixture is filtered, washed with 100 ml of ethyl acetate and the phases are separated. The organic phase is dried over MgSO4 , filtered, and the filtrate is freed from solvent on a rotary evaporator at a bath temperature of 60° C., giving 168.5 g (99% of theory) of colourless glycidyl ether of 4-methylcyclohexanol having the following properties: epoxy value: 4.93 eq/kg (84% of theory); total chlorine content: 4.75%; concentration of hydrolisable chlorine: 5900 ppm. In a 750 ml sulfonation flask equipped with thermometer reflux condenser, N2 inlet to react for 3 h After cooling to 50° C. the reaction mixture is filtered washed with 100 ml of ethyl acetate the phases are separated The organic phase is dried over MgSO4 filtered the filtrate is freed from solvent on a rotary evaporator at a bath temperature of 60° C.

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 750 ml sulfonation flask equipped with thermometer, reflux condenser, N2 inlet and metering device is charged with 114.19 g (1.0 mol) of 4-methylcyclohexanol and 1.7 g of catalyst A and the reaction mixture is heated to 100° C. With efficient stirring, 98.0 ml (1.25 mol) of epichlorohydrin are added, and the reaction mixture is thereafter allowed to react for 4 h. After cooling to 50° C., 1 g of tetramethylammonium chloride is added and to the solution are then added 8 g (0.1 mol) of a 50% aqueous solution of NaOH over 5 min, followed by the addition of 42 g (1.05 mol) of pulverised NaOH in increments over 45 min and the suspension is stirred for 5 h. After addition of 200 ml of ethyl acetate, the reaction mixture is filtered, washed with 100 ml of ethyl acetate and the phases are separated. The organic phase is dried over MgSO 4, filtered, and the filtrate is freed from solvent on a rotary evaporator at a bath temperature of 60° C., giving 170.7 g (100% of theory) of colourless glycidyl ether of 4-methylcyclohexanol having the following properties: epoxy value: 5.00 eq/kg (85% of theory); total chlorine content: 5.0%; concentration of hydrolisable chlorine: 3000 ppm. A 750 ml sulfonation flask equipped with thermometer reflux condenser, N2 inlet to react for 4 h After cooling to 50° C. the reaction mixture is filtered washed with 100 ml of ethyl acetate the phases are separated The organic phase is dried over MgSO 4 filtered the filtrate is freed from solvent on a rotary evaporator at a bath temperature of 60° C.