* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With hydroxylamine hydrochloride; hydroxylamine; potassium carbonate; In methanol; ethyl acetate;
EXAMPLE 1 28 Grams of hydroxylamine hydrochloride and 56 g of potassium carbonate were added in 400 ml of methanol, and the mixture was refluxed by hetting for 30 minutes. After cooling the reaction mixture to a room temperature, the supernatant liquor was collected by separation to prepare a methanol solution of hydroxylamine. To this methanol solution of hydroxylamine was added 16.2 g of <strong>[67901-82-0]7-hydroxy-4-methyl-1-indanone</strong> and refluxed by heating for 5 hours under stirring condition. The reaction mixture was concentrated to dryness under a reduced pressure. To the residue thus obtained was added 200 ml of ethyl acetate, then the insoluble matter was removed by filtration. The filtrate was concentrated to dryness under a reduced pressure, and the residue was recrystallized from methanol to obtain 17.6 g of <strong>[67901-82-0]7-hydroxy-4-methyl-1-indanone</strong> oxime in the form of colorless needle-like crystals. Melting point: 148-149.5 C.
With nitric acid; acetic anhydride; In acetic acid;
REFERENCE EXAMPLE 2 Into a solution of 25.6 g of <strong>[67901-82-0]4-methyl-7-hydroxy-1-indanone</strong> in 250 ml of acetic acid was added 19.4 ml of acetic anhydride and a solution of 15.4 ml of concentrated nitric acid in 50 ml of acetic acid gradually. The reaction mixture was concentrated to drynsss, and the residue was washed with ether to obtain 25.7 g of 4-methyl-6-nitro-7-hydroxy-1-indanone.
REFERENCE EXAMPLE 6 Into a solution of 36 g of <strong>[67901-82-0]4-methyl-7-hydroxy-1-indanone</strong> and 17.6 g of potassium hydroxide in 650 ml of methanol was added 25 ml of allyl bromide, and the mixture was refluxed by heating for 6 hours. The insoluble matters in the reaction mixture were removed by filtration, then the solvent was removed by evaporation. The residue obtained was extracted with chloroform-water, and the chloroform layer was collected by separation, then the solvent was removed by evaporation. The residue thus obtained was washed with ether and purified by means of a column chromatography to obtain 32 g of 4-methyl-7-allyloxy-1-indanone.
REFERENCE EXAMPLE 10 Into a solution of 15 g of <strong>[67901-82-0]4-methyl-7-hydroxy-1-indanone</strong> and 7.95 g of potassium hydroxide in 200 ml of methanol was added 13.55 ml of methallyl chloride, and the mixture was refluxed by heating for 11 hours. The insoluble matters in the reaction mixture were removed by filtration, then the solvent was removed by evaporation. The residue obtained was purified by means of a silica gel column chromatography (eluent: n-hexane: dichloromethane=1:1) to obtain 9 g of 4-methyl-7-methallyloxy-1-indanone.
7-hydroxy-4-methyl-6-(1-piperidinesulfonyl)-1-indanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
aluminium trichloride; In 1,1-dichloroethane;
REFERENCE EXAMPLE 16 Into a solution of 2 g of <strong>[67901-82-0]7-hydroxy-4-methyl-1-indanone</strong> in 10 ml of dichloroethane was added 2.27 g of 1-piperidine sulfonyl chloride. Then 10 g of anhydrous aluminum chloride was gradually added to the mixture and stirred, and the reaction mixture was refluxed by heating for 8 hours. The reaction mixture was extracted with 200 ml of chloroform, washed with water, then the chloroform was removed by evaporation under a reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent: chloroform), and recrystallized from ethanol to obtain 1.24 g of 7-hydroxy-4-methyl-6-(1-piperidinesulfonyl)-1-indanone.
REFERENCE EXAMPLE 8 Into a solution of 10 g of <strong>[67901-82-0]4-methyl-7-hydroxy-1-indanone</strong> and 5.3 g of potassium hydroxide in 200 ml of methanol was added 8.2 ml of crotyl bromide, and the mixture was refluxed by heating for 4 hours. The insoluble matters in the reaction mixture were removed by filtration, then the solvent was removed by evaporation. The residue obtained was extracted with chloroform-water, and the chloroform layer was washed with a diluted sodium hydroxide aqueous solution, then washed with water, dried with anhydrous magnesium sulfate, and the solvent was removed by evaporation. The residue obtained was purified by means of a silica gel column chromatography (eluent: n-hexane: dichloromethane=1:1) to obtain 8.72 g of 4-methyl-7-crotyloxy-1-indanone.
7-hydroxy-6-chlorosulfonyl-4-methyl-1-indanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With chlorosulfonic acid; In tetrachloromethane; ice-water;
REFERENCE EXAMPLE 15 Into a solution of 90 ml of chlorosulfonic acid in 150 ml of carbon tetrachloride was added 30 g of <strong>[67901-82-0]7-hydroxy-4-methyl-1-indanone</strong> gradually under an ice-cooling condition. The carbon tetrachloride layer was removed by separation, and one liter of ice-water was added into the residual layer then the mixture was stirred vigorously. The solid matter precipitated was collected by filtration, then washed with water to obtain 8.7 g of 7-hydroxy-6-chlorosulfonyl-4-methyl-1-indanone.
EXAMPLE 9 Preparation of O-Ethyl S-Propyl O-(4-methylindan-1-on-7-yl) Thiophosphate S-n-Propyl dichlorothiophosphate (3.6 grams; 0.0186 mole) and dry toluene (80 ml) were charged into a glass reaction vessel equipped with a magnetic stirrer, thermometer, addition funnel and gas inlet tube. The reaction vessel was purged with nitrogen gas and the reaction mixture was cooled to -10 C., Ethanol (0.085 gram; 0.0186 mole) and triethylamine (2.5 grams) dissolved in dry toluene (20 ml) was then added dropwise, with stirring, while maintaining the temperature of the reaction mixture below 0 C. After the addition was completed stirring was continued for a period of 5 hours while maintaining the temperature at 0 C. After this time <strong>[67901-82-0]4-methyl-7-hydroxyindan-1-one</strong> (3.0 grams; 0.0185 mole) dissolved in toluene (20 ml) and triethylamine (2.5 grams) dissolved in a small amount of methylene chloride were added dropwise with stirring at 0 C. After the addition was completed stirring was continued at room temperature overnight. The reaction mixture was then filtered and the filtrate washed with water. The washed solution was dried and stripped of solvent leaving an oil as the residue. This residue was chromatographed using a 150 ml clay column and mixtures of ethyl acetate and hexane as the eluant. Ten separate fractions were collected. Fractions 6 to 9 were combined, stripped of solvent and subjected to vacuum to yield the desired product O-ethyl S-propyl O-(4-methylindan-1-on-7-yl) thiophosphate as a yellow oil.
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