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Hydrochloric Acid → (E)-2,4-Dichloro-6-phenylmethoxycinnamaldehyde

HRID 1285588
ノート
印刷プレビュー

反応式

HRID 1285588 の反応式
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1[CH:4]=O.[OH-].[K+].[C:21](OC(=O)C)(=[O:23])[CH3:22].Cl>C(=O)C.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]=1/[CH:4]=[CH:22]/[CH:21]=[O:23]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 128028812,4-Dichloro-6-phenylmethoxybenzaldehyde

生成物 1

HCID 12802888(E)-2,4-Dichloro-6-phenylmethoxycinnamaldehyde収率 33%

試薬・触媒・溶媒 2

HCID 177Acetaldehyde
溶媒
HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

A stirred suspension of 2,4-dichloro-6-phenylmethoxybenzaldehyde (15.5 g, 55.1 mmole) in acetaldehyde (30 ml) was cooled to 5° C. and treated with 25% methanolic potassium hydroxide (1.4 ml, 6.24 mmole) at such a rate that the internal temperature was maintained at 25°-30° C. The resulting solution was stirred for 30 minutes in the ice bath, treated with acetic anhydride (30 ml) and then heated at 100° C. for 30 minutes. After cooling to 30° C. the solution was treated with water (84 ml) and 12N hydrochloric acid (7 ml). The resulting mixture was refluxed for 30 minutes and then cooled in an ice bath to give a gummy solid which was recrystallized from cyclohexane to give the title compound (5.6 g, 33%), mp 109°-112° C.: pmr (CDCl3) δ 5.10 (2H, s), 7.33 (5H, s), 9.68 (H, d).

後処理

  1. temperaturewas maintained at 25°-30° C
  2. temperatureheated at 100° C. for 30 minutes
  3. temperatureAfter cooling to 30° C. the solution
  4. temperatureThe resulting mixture was refluxed for 30 minutes
  5. temperaturecooled in an ice bath
  6. customto give a gummy solid which
  7. customwas recrystallized from cyclohexane

出典と根拠

ORDレコード
ord-c34cc49b8cd24df28ef7c7997dd072e4
出典データセット
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04567289

反応ノート

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