関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Iodide | HCID 5238 | — |
| 反応物 | Allyl bromide | HCID 7841 | — |
| 反応物 | 3-Chloro-2-methyl-1-propene | HCID 11241 | — |
| 反応物 | Potassium Hydroxide | HCID 14797 | — |
| 反応物 | 2-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate | HCID 23698133 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 生成物 | 4-Allyloxymandelic acid | HCID 19930564 | 70% |
| 生成物 | 4-Methallyloxymandelic acid | HCID 19930566 | — |
反応手順
20.8 g (0.10 mol) of 4-hydroxymandelic acid sodium salt monohydrate and 6.6 g (0.10 mol) of potassium hydroxide are dissolved with 1.0 g (6.7 mmol) of sodium iodide in 75 ml of methanol. Then 0.12 mol of allyl bromide (methallyl chloride in the case of methallyl) is added and the reaction mixture is refluxed for 16 hours under nitrogen. The reaction mixture is concentrated on a vacuum rotary evaporator and the residue is acidified with concentrated hydrochloric acid. The product is extracted 3 times with butyl acetate. The organic phases are washed with water, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from toluene/petroleum ether give 4-allyloxymandelic acids such as 4-allyloxymandelic acid as an amorphous powder (70%) and 4-methallyloxymandelic acid, m.p. 121°-126° (65%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US05428177 |
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| 出典データセット | uspto-grants-1995_06 |
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| ORD ID | ord-c5f188d297c44361a81bdec3606b483a |
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| 出典メモ | uspto-grants-1995_06 |
|---|
