Chlorosulfonic acid → 7-Hydroxy-6-chlorosulfonyl-4-methyl-1-indanone

Into a solution of 90 ml of chlorosulfonic acid in 150 ml of carbon tetrachloride was added 30 g of 7-hydroxy-4-methyl-1-indanone 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. This product was added, without purified, to a solution consisting of 31.4 g of stannous chloride dihydrate and 100 ml of concentrated hydrochloric acid, and the mixture was stirred at a room temperature for 4 hours. The reaction mixture was poured into 500 ml of ice-water, the crystals precipitated were collected by filtration, washed with water, dried to obtain 7.86 g of 7-hydroxy-6-mercapto-4-methyl-1-indanone. Next, this product was suspended, without purified, in 100 ml of methanol, then to this suspension was added 3.9 ml of methyl iodide and a solution of 5.1 g of sodium bicarbonate in 20 ml of water, the whole mixture was stirred at a room temperature for 1 hour. The mixture was concentrated under a reduced pressure to remove the solvent to dryness. The residue was purified by means of a silica gel column chromatography (eluent: chloroform) and recrystallized from ethanol to obtain 1.52 g of 7-hydroxy-4-methyl-6-methylthio-1-indanone.

1. temperaturecooling condition
2. customThe carbon tetrachloride layer was removed by separation, and one liter of ice-water
3. additionwas added into the residual layer
4. customThe solid matter precipitated
5. filtrationwas collected by filtration
6. washwashed with water

ORD 기록

ord-ee4378ed482f4225aec302670aa1be6d

출처 데이터셋

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04792628