関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Toluene | HCID 1140 | — |
| 反応物 | 3-Chloro-2-methyl-1-propene | HCID 11241 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 1-(3,3-Dimethylcyclohexyl)ethanone | HCID 91388 | — |
| 触媒 | Trioctylmethylammonium chloride | HCID 21218 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 1-(3,3-Dimethylcyclohexyl)ethanone | HCID 91388 | — |
| 生成物 | 1-Acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl)cyclohexane | HCID 20384605 | 5% |
| 生成物 | 3,3-Dimethyl-1-(2-methallyl-5-methyl-4-pentenoyl)cyclohexane | HCID 54015233 | — |
反応手順
A slurry of 1-acetyl-3,3-dimethylcyclohexane (624 grams, 4 moles), granular sodium hydroxide (240 grams, 6 moles), Aliquot® 336 (tricaprylmethylammonium chloride [35 grams]), methallyl chloride (432 grams, 4.8 moles), and 400 ml of toluene is heated at reflux for 41/4 hours. At the end of this time, one liter of water is added to the cooled reaction mass. The aqueous layer is discarded, and the organic layer is distilled rapidly through a short column to afford 203 grams of recovered 1-acetyl-3,3-dimethylcyclohexane, 500 grams of 1-acetyl-3,3-dimethyl-1-methallylcyclohexane (104°, 3.0 mm Hg, containing 5% 3,3-dimethyl-(4-methyl-4-pentenoyl)cyclohexane) and 73 grams of 3,3-dimethyl-1-(2-methallyl-5-methyl-4-pentenoyl) cyclohexane. A portion of the latter compound is isolated by GLC chromatography (1' × 1/4 inch 80% SE-30 packed column; 200° C. isothermal) and exhibits the following odor and flavor properties.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US04102928 |
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| 出典データセット | uspto-grants-1978_07 |
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| ORD ID | ord-0df0f149293c4311a0c530a892b4933b |
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| 出典メモ | uspto-grants-1978_07 |
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