octoxybenzene

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:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 22.2 g (or 0.057 mol) of hydroxytosyloxyiodobenzene, 9 g (or 0.04 mol) of n-octyl phenyl ether, 5 ml of acetonitrile and 1.5 ml of acetic acid were charged into a 250 ml Erlenmeyer flask equipped with a magnetic stirrer bar. This mixture was stirred and was heated to a temperature of 40° C. for 2 hours, 30 minutes. 1.5 ml of glacial acetic acid was then added and the mixture was then maintained for 5 hours at 40° C. The reaction mixture was permitted to cool and 150 ml of water were added while stirring vigorously. This mixture was then stirred for 12 hours at room temperature and was then separated. The organic phase was washed several times with water, until a yellow precipitate appeared. This solid was recovered by filtration, was washed with 50 ml of ether and was then dried under vacuum at a temperature of 45° C. equipped with a magnetic stirrer bar the mixture was then maintained for 5 hours at 40° C to cool while stirring vigorously This mixture was then stirred for 12 hours at room temperature was then separated The organic phase was washed several times with water This solid was recovered by filtration was washed with 50 ml of ether was then dried under vacuum at a temperature of 45° C.

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

実験手順: 44.8 g (or 0,477 mol) of phenol, 38.6 g (or 0.2 mol) of n-bromooctane, 6 g of tetrabutylammonium bromide, 26.8 g of potassium hydroxide, 100 ml of water and 100 ml of toluene were charged into a 500 ml, three-necked, round-bottom flask equipped with a mechanical stirrer, a thermometer and water-cooled reflux condenser. This medium was stirred and was then heated to reflux for 20 hours. The reaction mixture was then cooled to room temperature. The phases were settled and separated. The organic phase was washed with 100 ml of a 0.5N sodium hydroxide solution and then with five 100 ml fractions of water. It was then dried over magnesium sulfate and the solvent was then driven off under reduced pressure at a temperature of 85° C. three-necked, round-bottom flask equipped with a mechanical stirrer reflux condenser was then heated to reflux for 20 hours separated The organic phase was washed with 100 ml of a 0.5N sodium hydroxide solution It was then dried over magnesium sulfate was then driven off under reduced pressure at a temperature of 85° C.

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

実験手順: 44.8 g (or 0,477 mol) of phenol, 38.6 g (or 0.2 mol) of n-bromooctane, 6 g of tetrabutylammonium bromide, 26.8 g of potassium hydroxide, 100 ml of water and 100 ml of toluene were charged into a 500 ml, three-necked, round-bottom flask equipped with a mechanical stirrer, a thermometer and water-cooled reflux condenser. This medium was stirred and was then heated to reflux for 20 hours. The reaction mixture was then cooled to room temperature. The phases were settled and separated. The organic phase was washed with 100 ml of a 0.5N sodium hydroxide solution and then with five 100 ml fractions of water. It was then dried over magnesium sulfate and the solvent was then driven off under reduced pressure at a temperature of 85° C. three-necked, round-bottom flask equipped with a mechanical stirrer reflux condenser was then heated to reflux for 20 hours separated The organic phase was washed with 100 ml of a 0.5N sodium hydroxide solution It was then dried over magnesium sulfate was then driven off under reduced pressure at a temperature of 85° C.

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

実験手順: effecting reaction between phenol and 1-bromo octane in the presence of an aqueous basic solution and a phase transfer catalyst to form n-octylphenyl ether,

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

実験手順: effecting reaction between phenol and a-bromo octane in the presence of an aqueous basic solution and a phase transfer catalyst to form n-octylphenyl ether,

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

実験手順: A mixture of 224 grams (3 mols) of phenol in the form of a 88% aqueous solution, 193 grams (1 mol) of 1-bromooctane, 30 grams of tetra-n-butylammonium bromide, 224 grams (3 mols) of potassium hydroxide pellets, 500 ml of water and 500 ml of toluene was stirred under a nitrogen atmosphere while it was reflexing for a period of 16 hours. The reaction mixture was allowed to cool and the organic phase was washed with 500 ml, 0.5N sodium hydroxide to remove excess phenol. The toluene layer was washed with two 500 ml portions of water and the toluene was removed using a rotary evaporator. A quantitative yield of 98% pure octylphenyl ether was obtained based on gas chromotogrpahy and method of preparation. to cool the organic phase was washed with 500 ml, 0.5N sodium hydroxide to remove excess phenol The toluene layer was washed with two 500 ml portions of water the toluene was removed a rotary evaporator

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

実験手順: A 3-neck flask equipped with a thermometer, a nitrogen outlet and a mechanical stirrer, was charged with phosphorous pentoxide (8.64 g) followed by methanesulfonic acid (85.20 g). The resulting mixture was stirred at room temperature for 0.5 hour and then heated at 50° C. for 2-3 hours to obtain a homogeneous suspension. The mixture was cooled to below 10° C. in an ice-water bath and n-octylphenyl ether (21.66 g, 0.105 mol) was added. Next, p-tolylsulfoxide (20.03 g, 0.10 mol) was added with good stirring while maintaining the temperature of the reaction below 10° C. After stirring for 1 hour, the cooling bath was removed and the reaction was stirred at room temperature for 16 hours. Thereafter, the reaction mixture was added dropwise to a mixture of ice-water (500 mL) with vigorous stirring. The aqueous mixture was washed with toluene/hexane (3×100 mL, 1:1) and extracted with dichloromethane (3×200 mL). The combined organic layers were treated with an aqueous solution of ammonium 10-camphorsulfonate (prepared by neutralization of 10-camphorsulfonic acid (29.04 g, 0.125 mol) with ammonium hydroxide (14.53M, 8.6 mL, 0.125 mol)). The two phase solution was stirred at room temperature for 16 hours. The layers were separated and the aqueous phase extracted with dichloromethane (3×200 mL). The combined organic layers were washed with water (3×200 mL) and concentrated in vacuo to give a dark oil which solidified on standing to give a lightly colored solid @ 65 g. The solid was triturated in ether-ethylacetate for 18 hours, collected by suction filtration and dried in vacuo to provide the title compound, di-(4-tolyl)-4-octyloxyphenylsulfonium 10-camphorsulfonate, as a white solid. A 3-neck flask equipped with a thermometer, a nitrogen outlet and a mechanical stirrer heated at 50° C. for 2-3 hours to obtain a homogeneous suspension The mixture was cooled to below 10° C. in an ice-water bath with good stirring while maintaining the temperature of the reaction below 10° C After stirring for 1 hour the cooling bath was removed the reaction was stirred at room temperature for 16 hours Thereafter, the reaction mixture was added dropwise to a mixture of ice-water (500 mL) with vigorous stirring The aqueous mixture was washed with toluene/hexane (3×100 mL, 1:1) extracted with dichloromethane (3×200 mL) The two phase solution was stirred at room temperature for 16 hours The layers were separated the aqueous phase extracted with dichloromethane (3×200 mL) The combined organic layers were washed with water (3×200 mL) concentrated in vacuo to give a dark oil which to give a lightly colored solid @ 65 g The solid was triturated in ether-ethylacetate for 18 hours collected by suction filtration dried in vacuo

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

実験手順: A sample of (4-octyloxyphenyl)phenyl iodonium toluenesulfonate (in short C8-O-iodonium) was prepared according to the method of Crivello et al (J. Polym. Sci: Part A: Polymer Chemistry, (1989), 27, 3951-3968) by reacting hydroxytosyloxyiodobenzene with octyloxybenzene in a mixture of acetonitrile and acetic acid. Octyloxybenzene was previously obtained by reacting sodium phenate with bromooctane in a water/toluene mixture by phase transfer catalysis in the presence of tetrabutyl ammonium bromide. To 8 g of this compound in solution in 60 ml of methylethylketone (MEK) are added 3.02 of potassium bis-fluorosulfonylimide. The mixture is stirred magnetically for 1 hour at room temperature and filtrated to remove the insoluble potassium toluenesulfonate. The solution is poured into a flask which is adjusted to be adapted on a rotary evaporator and the solvent is evaporated. The last traces of MEK are eliminated under a vacuum primary pump and the residue is in the form of a viscous oil (8.04 g, 98%). There is added thereto an equal weight of dichloromethane enabling to give a fluid mixture which can be handled. Solubility tests are made in adjusted flasks after adding a given quantity of mixture and evaporation of the volatile fraction (CH2Cl2). Results of the tests are given below:

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

実験手順: A sample of (4-octyloxyphenyl)phenyl iodonium toluenesulfonate (in short C8-O-iodonium) was prepared according to the method of Crivello et al (J. Polym. Sci: Part A: Polymer Chemistry, (1989), 27, 3951-3968) by reacting hydroxytosyloxyiodobenzene with octyloxybenzene in a mixture of acetonitrile and acetic acid. Octyloxybenzene was previously obtained by reacting sodium phenate with bromooctane in a water/toluene mixture by phase transfer catalysis in the presence of tetrabutyl ammonium bromide. To 8 g of this compound in solution in 60 ml of methylethylketone (MEK) are added 3.02 of potassium bis-fluorosulfonylimide. The mixture is stirred magnetically for 1 hour at room temperature and filtrated to remove the insoluble potassium toluenesulfonate. The solution is poured into a flask which is adjusted to be adapted on a rotary evaporator and the solvent is evaporated. The last traces of MEK are eliminated under a vacuum primary pump and the residue is in the form of a viscous oil (8.04 g, 98%). There is added thereto an equal weight of dichloromethane enabling to give a fluid mixture which can be handled. Solubility tests are made in adjusted flasks after adding a given quantity of mixture and evaporation of the volatile fraction (CH2Cl2). Results of the tests are given below:

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: n-Octyloxybenzene (301 g, 1.46 mol), succinic anhydride (146.8 g, 1.468 mol) and carbon disulfide (1.3 l) were agitated at room temperature, followed by portion-wise feeding anhydrous aluminum chloride (392 g, 2.94 mol), further agitating the mixture at 50° C. for 4 hours after the reaction became quiet, cooling the mixture down to room temperature, adding it to ice (2 Kg), distilling off carbon disulfide, collecting solids, adding toluene (1 l), distilling off water on heating, filtering while hot, and distilling off toluene under reduced pressure to obtain oily β-(p-octyloxybenzoyl)-propionic acid (238 g, yield 53%). cooling the mixture down to room temperature distilling off carbon disulfide collecting solids adding toluene (1 l) distilling off water on heating filtering while hot, and distilling off toluene under reduced pressure