(E)-3,3′-Dimethoxy-4,4′-dihydroxystilbene → 4,4'-(Ethane-1,2-diyl)bis(2-methoxyphenol)

HRID 531401Notes

Reaction equation

HRID 531401 reaction equation
[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

Participants

4

Reactant 1

HCID 5280698(E)-3,3′-Dimethoxy-4,4′-dihydroxystilbene

Product 1

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

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6ef9bd1369ab4bb4996b71198a1f0d62
Source dataset
uspto-grants-2016_05
Patent number
US09353219B1

Reaction notes

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