化工社化工社 化学情報印刷レポート · 研究参考用
Formaldehyde → 3-Phenoxyprop-2-enal
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Formaldehyde | HCID 712 | — |
| 反応物 | (Diethoxyphosphinyl)acetic acid | HCID 36704 | — |
| 反応物 | Phenoxyacetaldehyde | HCID 75033 | — |
| 反応物 | Diethylammonium chloride | HCID 10197650 | — |
| 反応物 | Butyllithium | HCID 178418339 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 3-Phenoxyprop-2-enal | HCID 54307207 | — |
| 生成物 | 5-Phenoxy-2,4-pentadienoic acid | HCID 73863370 | — |
反応手順
2-Formylvinyl phenyl ether is prepared by treating phenoxyacetaldehyde with formaldehyde and diethylamine hydrochloride salt. The ether is then reacting with a solution of diethylphosphonoacetic acid and n-butyllithium in anhydrous tetrahydrofuran (THF) to form 5-phenoxy-2,4-pentadienoic acid. 5-Phenyl-2,4-pentadienal is obtained by first converting the carboxylic acid to a Weinreb amide using oxalyl chloride followed by N,O-dimethylhydroxylamine. Subsequently, reduction of the Weinreb amide with lithium aluminum hydride (LAH) in THF leads to the formation of 5-phenoxy-2,4-pentadienal. The synthesis is summarized in Scheme II.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07579372B2 |
| 出典データセット | uspto-grants-2009_08 |
| ORD ID | ord-760afae2ebd147e1985a5c120b3f69f7 |
| 出典メモ | uspto-grants-2009_08 |