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

HRID 1660547
ノート
印刷プレビュー

反応式

HRID 1660547 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 12 N 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) δ5.10 (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-78043792cc794581879100f484c2bc77
出典データセット
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04308378

反応ノート

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