butyl 2-hydroxybenzoate

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

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

Procedure: 4-Chloro-6,7-dimethoxyquinoline (100 mg), butyl salicylate (388 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight and at 140° C. for 3 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then 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 (106 mg, yield 57%). The reaction solution was cooled to room temperature the solvent was removed by distillation under the reduced pressure Water was then 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:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-6,7-dimethoxyquinoline (100 mg), butyl salicylate (388 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight and at 140° C. for 3 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then 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 (106 mg, yield 57%). The reaction solution was cooled to room temperature the solvent was removed by distillation under the reduced pressure Water was then 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:

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

Procedure: A 5.8 g portion of n-butyl salicylate was added to a solution of 1.2 g of sodium hydroxide in 75 ml of water, producing a thick suspension. To the above suspension was added 100 ml of methylene chloride and 0.3 g of tricaprylylmethyl ammonium chloride. The reaction mixture was stirred vigorously while a solution of 8.1 g of methyl N-[[N-[(fluorocarbonyl-N-methylamino)thio]-N-methylaminocarbonyloxy]]ethanimidothioate in 50 ml methylene chloride was added dropwise. When addition was complete, stirring was continued for one hour. The organic phase was separated and washed with 200 ml of water followed by 100 ml of saturated sodium chloride solution. The organic solution was dried over anhydrous magnesium sulfate, and the solvent was distilled under reduced pressure. On scratching and standing, the crude reaction product partially solidified. The title compound was isolated by dissolving the crude reaction product in 25 ml of ethanol, cooling the solution and diluting with hexane to afford 5.7 g of 2-[N-methyl-N-[N-methyl-N-[(1-methylthioethylidene)aminooxycarbonyl]aminothio]aminocarbonyloxy]benzoic acid butyl ester, m.p. 87° -89° C. Absorption bands characteristic of the title compound were observed in the infrared and NMR spectrums. producing a thick suspension was added dropwise When addition The organic phase was separated washed with 200 ml of water The organic solution was dried over anhydrous magnesium sulfate the solvent was distilled under reduced pressure the crude reaction product

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Continuing, the resulted white powder was placed in a 100 ml eggplant type flask to which was then added a Teflon™-coated stirring bar and 100 ml of dioxane. 1.68 (15 millimoles) of potassium t-butyldicarbonate were added in a nitrogen atmosphere and stirred for 4 hours at 0° C. 3 g (13.9 millimoles) of di-t-butyldicarbonate were then added followed by additionally stirring for 3 hours at 0° C. After concentrating the reaction solution, it was dropped in 1.5 liters of methanol resulting in precipitation. The formed precipitate was filtered off with a glass filter and dried for 16 hours at 0.1 mmHg and 45° C. The resulted white powder was dissolved in THF, and the above-mentioned precipitation and drying procedure was repeated twice to obtain a white resin powder. When the composition of this white powder was examined by 1H-NMR, the ratio of phenol to butoxycarbonylphenol to methacrylate in the copolymer was determined to be 31:39:30. The transmittance of this copolymer at a wavelength of 248 nm was 60% (film thickness: 1 μm, on a quartz substrate), thus indicating excellent transparency. In addition, other analysis results were as shown below. the resulted white powder was placed in a 100 ml eggplant type flask to which was then added a Teflon™-coated stirring bar by additionally stirring for 3 hours at 0° C After concentrating the reaction solution, it was dropped in 1.5 liters of methanol resulting in precipitation The formed precipitate was filtered off with a glass filter dried for 16 hours at 0.1 mmHg and 45° C The resulted white powder was dissolved in THF the above-mentioned precipitation drying procedure to obtain a white resin powder In addition, other analysis results

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

Procedure: 4-Chloro-6,7-dimethoxyquinoline (100 mg), butyl salicylate (388 mg), and 4-dimethylaminopyridine (244 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight and at 140° C. for 3 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then 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 (106 mg, yield 57%). The reaction solution was cooled to room temperature the solvent was removed by distillation under the reduced pressure Water was then 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