7-hydroxy-2,2,8-trimethyl-3H-chromen-4-one

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

Procedure: The reaction is carried out under nitrogen. In 50 ml of a 10% sodium hydroxide solution 4.9 g (23.8 millimoles) of 7-hydroxy-2,2,8-trimethyl-4-chromanone are dissolved, 2.6 g (2 ml, 21 millimoles) of dimethyl sulfate are added and the reaction mixture is vigorously stirred for 2 hours. The reaction mixture is diluted with 100 ml of icecold water and extracted three times with 50 ml of carbon tetrachloride each. The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate, the solvent is removed and the residue crystallized from 90% methanol. Thus 3.4 g of the desired compound are obtained, yield 78%. Mp.: 105°-107° C. extracted three times with 50 ml of carbon tetrachloride each The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate the solvent is removed the residue crystallized from 90% methanol

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

Procedure: The reaction is carried out under nitrogen. In 50 ml of a 10% sodium hydroxide solution 4.9 g (23.8 millimoles) of 7-hydroxy-2,2,8-trimethyl-4-chromanone are dissolved, 2.6 g (2 ml, 21 millimoles) of dimethyl sulfate are added and the reaction mixture is vigorously stirred for 2 hours. The reaction mixture is diluted with 100 ml of icecold water and extracted three times with 50 ml of carbon tetrachloride each. The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate, the solvent is removed and the residue crystallized from 90% methanol. Thus 3.4 g of the desired compound are obtained, yield 78%. Mp.: 105°-107° C. extracted three times with 50 ml of carbon tetrachloride each The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate the solvent is removed the residue crystallized from 90% methanol

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

Procedure: The mixture of 10.3 g. of the compound obtained in (1), 8.2 g. of benzyl chloride, 10.2 g. of potassium carbonate, 0.5 g. of potassium iodide, and 100 ml of acetone was refluxed for 2 hours. The mixture was then filtered, and the filtrate was concentrated. Ether was added to the concentrate. The ether layer was washed successively with water, 1 N aqueous sodium hydroxide, and again with water. The solution was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane, to obtain 12.2 g. (yield: 82.4%) of the subject compound. The mixture of 10.3 g The mixture was then filtered the filtrate was concentrated Ether was added to the concentrate The ether layer was washed successively with water, 1 N aqueous sodium hydroxide The solution was dried over magnesium sulfate the solvent was distilled off under reduced pressure The residue was recrystallized from ethyl acetate/n-hexane to obtain 12.2 g

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

Procedure: The reaction is carried out under nitrogen. In 50 ml of a 10% sodium hydroxide solution 4.9 g (20 millimoles) of 7-hydroxy-2,2,8-trimethyl-4-chromanone are dissolved, 2.6 g (2 ml, 21 millimoles) of dimethyl sulfate are added and the reaction mixture is vigorously stirred for 2 hours. The reaction mixture is diluted with 100 ml of icecold water and extracted three times with 50 ml of carbon tetrachloride each. The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate, the solvent is removed and the residue crystallized from 90% methanol. Thus 3.4 g of the desired compound are obtained, yield 78%. Mp.: 105°-107° C. extracted three times with 50 ml of carbon tetrachloride each The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate the solvent is removed the residue crystallized from 90% methanol

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

Procedure: The reaction is carried out under nitrogen. In 50 ml of a 10% sodium hydroxide solution 4.9 g (23.8 millimoles) of 7-hydroxy-2,2,8-trimethyl-4-chromanone are dissolved, 2.6 g (2 ml, 21 millimoles) of dimethyl sulfate are added and the reaction mixture is vigorously stirred for 2 hours. The reaction mixture is diluted with 100 ml of icecold water and extracted three times with 50 ml of carbon tetrachloride each. The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate, the solvent is removed and the residue crystallized from 90% methanol. Thus 3.4 g of the desired compound are obtained, yield 78%. Mp.: 105°-107° C. extracted three times with 50 ml of carbon tetrachloride each The organic phase is washed twice with 50 ml of water each, dried over sodium sulfate the solvent is removed the residue crystallized from 90% methanol