2-prop-1-enylphenol

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: The preparation of 2-propenylphenol from phenol and allyl bromide is similar to that outlined1. The reaction of this compound with dibromomethane is similar to that described above for di (N-phenylcarboxaldimine-4-phenoxy)methane. The title compound was extracted with ether 3×100 ml portions from the aqueous dimethylformamide solution, washed with aqueous potassium hydroxide (10%) and then water. The ether phase was dried over sodium sulphate and the solvent was stripped off under reduced pressure. The oil which contained some (~5%) of a less polar component and at least two isomeric forms of the title compound, as indicated from high pressure liquid chromatography, was used without further purification in the reaction below. The title compound was extracted with ether 3×100 ml portions from the aqueous dimethylformamide solution washed with aqueous potassium hydroxide (10%) The ether phase was dried over sodium sulphate was used without further purification in the reaction below

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

Procedure: α,α'-bis-(2-propenylphenoxy)-meta-xylene is prepared in a process similar to Example I, except that 383 grams (2.86 mole) of propenylphenol is employed along with 250 grams (1.43 moles) of α,α'-dichloro-meta-xylene to give a reaction product extracted with methylene chloride, washed with potassium hydroxide and dried over magnesium sulfate, then vaccum distilled at 80° C. to yield 407 grams of a viscous liquid (80% yield). to give a reaction product extracted with methylene chloride washed with potassium hydroxide dried over magnesium sulfate vaccum distilled at 80° C.

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

Procedure: α,α'-bis-(2-propenylphenoxy)-meta-xylene is prepared in a process similar to Example I, except that 383 grams (2.86 mole) of propenylphenol is employed along with 250 grams (1.43 moles) of α,α'-dichloro-meta-xylene to give a reaction product extracted with methylene chloride, washed with potassium hydroxide and dried over magnesium sulfate, then vaccum distilled at 80° C. to yield 407 grams of a viscous liquid (80% yield). to give a reaction product extracted with methylene chloride washed with potassium hydroxide dried over magnesium sulfate vaccum distilled at 80° C.

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

Procedure: 1,3-bis(ortho-propenylphenoxy)propane is prepared in a procedure similar to Example I, except that 537 grams (4.0 moles) of propenyl phenol is employed along with 403 grams (1.98 moles) of 1,3-dibromo-propane to produce a reaction mixture extracted with methylene chloride and dried over magnesium sulfate, then vacuum distilled to give 311 grams (50% yield) of a solid with melting point 45°-48° C. to produce a reaction mixture extracted with methylene chloride dried over magnesium sulfate vacuum distilled

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

Procedure: The preparation of 2-propenylphenol from phenol and allyl bromide is similar to that outlined1. The reaction of this compound with dibromomethane is similar to that described above for di (N-phenylcarboxaldimine-4-phenoxy)methane. The title compound was extracted with ether 3×100 ml portions from the aqueous dimethylformamide solution, washed with aqueous potassium hydroxide (10%) and then water. The ether phase was dried over sodium sulphate and the solvent was stripped off under reduced pressure. The oil which contained some (~5%) of a less polar component and at least two isomeric forms of the title compound, as indicated from high pressure liquid chromatography, was used without further purification in the reaction below. The title compound was extracted with ether 3×100 ml portions from the aqueous dimethylformamide solution washed with aqueous potassium hydroxide (10%) The ether phase was dried over sodium sulphate was used without further purification in the reaction below

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

Procedure: The preparation of 2-propenylphenol from phenol and allyl bromide is similar to that outlined1. The reaction of this compound with dibromomethane is similar to that described above for di (N-phenylcarboxaldimine-4-phenoxy)methane. The title compound was extracted with ether 3×100 ml portions from the aqueous dimethylformamide solution, washed with aqueous potassium hydroxide (10%) and then water. The ether phase was dried over sodium sulphate and the solvent was stripped off under reduced pressure. The oil which contained some (~5%) of a less polar component and at least two isomeric forms of the title compound, as indicated from high pressure liquid chromatography, was used without further purification in the reaction below. The title compound was extracted with ether 3×100 ml portions from the aqueous dimethylformamide solution washed with aqueous potassium hydroxide (10%) The ether phase was dried over sodium sulphate was used without further purification in the reaction below

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-6,7-dimethoxyquinoline (100 mg), 2-(1-propenyl)phenol (231 μl), and 4-dimethylaminopyridine (220 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 140° C. for 7 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Thereafter, water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (137 mg, yield 43%). The reaction solution was cooled to room temperature the solvent was then removed by distillation under the reduced pressure Thereafter, water was added to the residue the mixture was extracted with chloroform The chloroform layer was washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

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

Procedure: A mixture of 7.112 g (50.0 mmol) of 2-propenylphenol (E/Z mixture), 7.041 g of potassium carbonate (50.0 mmol) and 20 ml of acetone was stirred at the boiling point under reflux for 20 minutes. A mixture of 6.94 g (75.0 mmol) of chloroacetone, 0.171 g (1.0 mmol) of potassium iodide and 6.5 ml of acetone which had been activated beforehand by stirring overnight at room temperature was then added to the reaction mixture and the reaction mixture was stirred overnight at the boiling point under reflux. The reaction mixture was cooled to room temperature, added to 50 ml of water and extracted three times with 40 ml each time of diethyl ether. The organic phase was washed with 5% strength sodium hydroxide solution, separated off, dried over Na2SO4 and evaporated. Distillation of the crude product under reduced pressure gave 6.788 g (yield: 67% of theory) of 2-propenylphenyloxymethyl methyl ketone of the formula 2a: under reflux for 20 minutes by stirring overnight at room temperature was then added to the reaction mixture the reaction mixture was stirred overnight at the boiling point under reflux extracted three times with 40 ml each time of diethyl ether The organic phase was washed with 5% strength sodium hydroxide solution separated off dried over Na2SO4 evaporated Distillation of the crude product under reduced pressure

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-6,7-dimethoxyquinoline (100 mg), 2-(1-propenyl)phenol (231 μl), and 4-dimethylaminopyridine (220 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 140° C. for 7 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Thereafter, water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (137 mg, yield 43%). The reaction solution was cooled to room temperature the solvent was then removed by distillation under the reduced pressure Thereafter, water was added to the residue the mixture was extracted with chloroform The chloroform layer was washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography