(E)-4,4'-(ethene-1,2-diyl)bis(2-methoxyphenol) → 4,4'-(Ethane-1,2-diyl)bis(2-methoxyphenol)
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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).