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4-Nitrophenol → (E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester

HRID 1110520
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HRID 1110520 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[N+:24]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)([O-:26])=[O:25].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([O:14][C:13](=[O:15])/[CH:12]=[CH:11]/[CH:10]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)=[CH:29][CH:28]=1)([O-:26])=[O:25]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347253(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid

생성물 1

HCID 14347315(E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester수율 84.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

As in Example 115, (E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid (21.0 g) and 4-nitrophenol (11.2 g) in dichloromethane (300 mL) was treated with 1,3-dicyclohexylcarbodiimide (14 g). The mixture was stirred at 0°-5° C. for 1 hour, then at room temperature overnight. After the usual work up, the crude product was crystallized from ether-hexane to give 24.7 g of (E)-5,5-bis(4-methoxyphenyl)-2,4-pentadienoic acid 4-nitrophenyl ester mp 121°-123° C. Recrystallization of the material from 2-propanol afforded the purified ester, mp 125°-126° C. Anal. Calculated for C25H21NO6 : C, 69.60; H, 4.91; N, 3.23 Found: C, 69.19; H, 4.94; N, 3.25.

후처리

  1. customat room temperature
  2. customovernight
  3. customAfter the usual work up, the crude product was crystallized from ether-hexane

출처 및 근거

ORD 기록
ord-b600972cd81f4419b09b021671755ace
출처 데이터셋
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04975438

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