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

HRID 1285588
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HRID 1285588 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 177Acetaldehyde
용매
HCID 962Water용매

반응 조건

온도
5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c34cc49b8cd24df28ef7c7997dd072e4
출처 데이터셋
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04567289

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