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Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 9-(2-chloroethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) | HCID 6639 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one | HCID 607984 | — |
| 触媒 | Tetrabutylammonium hydrogen sulfate | HCID 94433 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 9-(2-chloroethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one | HCID 818594 | — |
反応手順
100 g. (0.5 mole) of 6-methyl-1,2,3,4-tetrahydrocarbazol-1-one and 234.5 g. (1 mole) of p-toluenesulfonic acid-β-chloroethylester are dissolved in 700 ml. of toluene and stirred together with a solution of 4.25 g. (12.5 m moles) of tetrabutylammoniumhydrogensulfate in 500 ml. of aqueous sodium hydroxide solution (30% strength) for 10 hours at room temperature. The organic layer is separated, washed with water and concentrated by evaporation. 108 g. (=83% of the theoretical) of 6-methyl-9-(2-chloroethyl)-1,2,3,4-tetrahydrocarbazol-1-one (melting at 106° to 107° C.) are thus obtained.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04258043 |
| 出典データセット | uspto-grants-1981_03 |
| ORD ID | ord-739c9d0811b2474db0f52f67dad9d8eb |
| 出典メモ | uspto-grants-1981_03 |