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(E)-4,4'-(ethene-1,2-diyl)bis(2-methoxyphenol) → 4,4'-(Ethane-1,2-diyl)bis(2-methoxyphenol)

HRID 531401
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HRID 531401 반응식
[CH:1](/[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1)=[CH:2]\[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([O:10][CH3:11])[CH:4]=1>O=[Pt]=O.C1COCC1>[CH2:1]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=1)[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([O:10][CH3:11])[CH:4]=1
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참가 물질

4

반응물 1

HCID 5280698(E)-4,4'-(ethene-1,2-diyl)bis(2-methoxyphenol)

생성물 1

HCID 148038254,4'-(Ethane-1,2-diyl)bis(2-methoxyphenol)수율 91%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8028Tetrahydrofuran용매

실험 절차

A Parr reaction vessel was charged with (E)-4,4′-(ethene-1,2-diyl)bis(2-methoxyphenol) (2.85 g, 10.5 mmol), THF (50 mL), PtO2 (70 mg), and then placed under hydrogen (30 psig) and allowed to react at ambient temperature for 16 h with continuous agitation. The mixture was filtered through glass wool to remove platinum and the THF was removed under reduced pressure. The solid was washed with hexanes (2×30 mL) and dried under reduced pressure to afford 2.62 g of light brown solid (91% yield). 1H NMR (DMSO-d6) δ 8.66 (s, 2H, Ph-OH), 6.73 (s, 2H), 6.65-6.53 (m, 4H), 3.70 (s, 6H, OMe), 2.70 (s, 4H, CH2); 13C NMR (DMSO-d6): δ 147.7, 144.9, 133.1, 120.9, 115.6, 113.1, 56.0 (OMe), 37.6 (CH2).

후처리

  1. customA Parr reaction vessel
  2. customto react at ambient temperature for 16 h with continuous agitation
  3. filtrationThe mixture was filtered through glass wool
  4. customto remove platinum
  5. customthe THF was removed under reduced pressure
  6. washThe solid was washed with hexanes (2×30 mL)
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-6ef9bd1369ab4bb4996b71198a1f0d62
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353219B1

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