4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) synthesis
- Product Name:4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE)
- CAS Number:7478-69-5
- Molecular formula:C18H22N2
- Molecular Weight:266.38
1779-49-3
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Yield: 92%
Reaction Conditions:
Stage #1:Methyltriphenylphosphonium bromide with potassium tert-butylate in tetrahydrofuran at 0; for 2 h;Inert atmosphere;
Stage #2:bis(p-dimethylaminophenyl)methanone in tetrahydrofuran at 0;Reflux;Wittig Olefination;
Steps:
2.3 Synthesis of 1,1-bis(4-dimethylaminophenyl)ethylene
The synthesis of BDADPE was conducted by the classic Wittig reaction using 4,4′-bis(dimethylamino)benzophenone as substrate under an argon atmosphere (described in detail by Hirao [29]). Typically, methyltriphenylphosphonium bromide (45.58g, 127.6mmol) and freshly distilled THF (500mL) were added into a round bottom flask equipped with a reflux condenser and a magnetic bar. Potassium tert-butoxide (138.4mL of a 1.0M solution in THF, 138.4mmol) was then added dropwise to the reaction flask via constant pressure funnel. The reaction mixture was stirred for 2h at 0°C. Then the solution of 4,4′-bis(dimethylamino)benzophenone (21.4g, 79.75mmol) in dry THF (690mL) was dropped to the reaction mixture via constant pressure funnel at 0°C. The orange-brown reaction mixture was heated to reflux for 7h with stirring and then quenched with distilled water. The resultant mixture was extracted with ether three times. Such ethereal layer was washed with aqueous NaHCO3 solution and saturated aqueous NaCl solution and then dried over MgSO4. After filtration, the ethereal layer was poured into hexane to precipitate triphenylphosphine oxide. Flash column chromatography (petroleum ether/ethyl acetate 2:1 v/v) gave BDADPE in 92% yield (19.52g, 73.37mmol) and Rf=0.76. 1H NMR (CDCl3, 400MHz): δ 2.96 (s, 12H, 2×N(CH3)2), 5.19 (s, 2H, CH2=C), 6.68-6.70 (d, 4H, aromatic proton ortho to N(CH3)2), 7.25-7.28 (d, 4H, aromatic proton meta to N(CH3)2).
References:
Wu, Lingling;Wang, Yanshai;Wang, Yurong;Shen, Kaihua;Li, Yang [Polymer,2013,vol. 54,# 12,p. 2958 - 2965]
78-08-0
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78-08-0
271 suppliers
$11.19/100G
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423 suppliers
$5.00/10g
7478-69-5
36 suppliers
$60.00/100mg
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7478-69-5
36 suppliers
$60.00/100mg
90-94-8
212 suppliers
$29.00/100g
7478-69-5
36 suppliers
$60.00/100mg