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Ethylene Glycol → 2-(4-Nitrophenyl)-1,3-dioxolane

HRID 888057
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HRID 888057 반응식
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]2[O:14][CH2:13][CH2:12][O:9]2)=[CH:10][CH:11]=1)([O-:3])=[O:2]
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참가 물질

5

반응물 3

HCID 174Ethylene GlycolHCID 5414-NitrobenzaldehydeHCID 6101p-Toluenesulfonic acid

생성물 1

HCID 2667962-(4-Nitrophenyl)-1,3-dioxolane수율 92.9%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
120 °C

실험 절차

In a 3-neck round-bottom flask equipped with Dean-Stark apparatus, reflux condenser and mechanical stirrer, p-nitrobenzaldehyde (101.5 g, 672 mmol), ethylene glycol (112 mL, 2.0 mol), and p-toluene sulfonic acid (12.8 g, 67.2 mmol, 10% mol) were suspended in toluene (800 mL) and then heated at 120° C. for 4 hours. The reaction mixture was cooled to room temperature and the toluene was removed under reduced pressure. Saturated aqueous sodium bicarbonate solution (800 mL) was added, and the resulting slurry was stirred at room temperature for 15 minutes, and then filtered and dried under vacuum to give the title compound (121.8 g) as a solid. 1H NMR (DMSO-d6): δ=8.12 (d, 2H), 7.59 (d 2H), 5.78 (s, 1H), 3.8-4.0 (m, 4H).

후처리

  1. customIn a 3-neck round-bottom flask equipped with Dean-Stark apparatus
  2. temperaturereflux condenser and mechanical stirrer
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe toluene was removed under reduced pressure
  5. additionSaturated aqueous sodium bicarbonate solution (800 mL) was added
  6. filtrationfiltered
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-5197c77e0b784db8b4ff4c6f81fbeb70
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08247564B2

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