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Acetic Acid → Dimethyl 3,3'-[(1,2-ethanediyl)bis(oxy)bis(3-methoxy-4,1-phenylene)bis(2-cyano-2-propenoate)]

HRID 982132
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HRID 982132 반응식
[CH2:1]([O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[O:23][CH3:24])[CH2:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][C:5]=1[O:12][CH3:13].[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])#[N:26].C[N:33]([CH3:36])C=O.N1CCCC[CH2:38]1.[C:43]([OH:46])(=[O:45])[CH3:44]>>[CH2:1]([O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[C:44]([C:36]#[N:33])[C:43]([O:46][CH3:38])=[O:45])=[CH:17][C:16]=1[O:23][CH3:24])[CH2:2][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:27]([C:25]#[N:26])[C:28]([O:30][CH3:31])=[O:29])=[CH:6][C:5]=1[O:12][CH3:13]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 30926074-[2-(4-Formyl-2-methoxyphenoxy)ethoxy]-3-methoxybenzaldehyde

생성물 1

HCID 54225960Dimethyl 3,3'-[(1,2-ethanediyl)bis(oxy)bis(3-methoxy-4,1-phenylene)bis(2-cyano-2-propenoate)]
수율 81%

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온도
100 °C

실험 절차

A mixture of 4,4'-[(1,2-ethanediyl)bis(oxy)bis(3-methoxybenzaldehyde)] (49.5 g, 0.15 mol), methyl cyanoacetate (30 g, 0.30 mol), N,N-dimethylformamide (500 mL), piperidine (3 mL) and acetic acid (1 mL) is heated with stirring at about 100° C. for 2 hours. The reaction mixture is allowed to cool to room temperature and the pale yellow solid which forms is collected by filtration and washed with methanol. The crude product is reslurried in 500 mL of boiling methanol, collected by filtration, washed with methanol and dried in air. A yield of 59.4 g (81% of theory) of dimethyl 3,3'-[(1,2-ethanediyl)bis(oxy)bis(3-methoxy-4,1-phenylene)bis(2-cyano-2-propenoate)] having the formula: ##STR14## is obtained. The bis-methine compound has an absorption maximum (λmax) at 365 nm in methylene chloride in the UV absorption spectrum (ε=46,856).

후처리

  1. temperatureis heated
  2. temperatureto cool to room temperature
  3. filtrationthe pale yellow solid which forms is collected by filtration
  4. washwashed with methanol
  5. filtrationcollected by filtration
  6. washwashed with methanol
  7. customdried in air

출처 및 근거

ORD 기록
ord-11b15e5f632e4521858f6f117dcb8f39
출처 데이터셋
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04994512

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