2,2,4,4-Pentanetetracarboxylic acid, 3-(4-nitrophenyl)-, 1,2,4,4-tetraethyl ester synthesis
- Product Name:2,2,4,4-Pentanetetracarboxylic acid, 3-(4-nitrophenyl)-, 1,2,4,4-tetraethyl ester
- CAS Number:126989-14-8
- Molecular formula:C21H27NO10
- Molecular Weight:453.44
![Propanedioic acid, 2-[(4-nitrophenyl)Methylene]-, 1,3-diethyl ester](/CAS/GIF/22399-00-4.gif)
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Yield:126989-14-8 93%
Reaction Conditions:
Stage #1: diethyl malonatewith sodium ethanolate in ethanol at 20; for 0.333333 h;
Stage #2: diethyl 4-nitrobenzylidene malonate in ethanol at 20; for 6 h;
Stage #3: with acetic acid in ethanol; for 0.0833333 h;
Steps:
1.f
f) 2,4-Bis-ethoxycarbonyl-3-(4-nitro-phenyl)-pentanedioic acid diethyl ester A solution of 1.42 g (20.8 mmol) of solid NaOEt in EtOH (30 mL) was treated with 3.43 mL (22.6 mmol) of malonic acid diethyl ester at RT for 20 min. This mixture was treated with a solution of 5.09 g (17.4 mmol) of 2-(4-nitro-benzylidine)-malonic acid diethyl ester (as prepared in the previous step) at RT for 6 h. AcOH (5 mL) was added, and the mixture stirred for 5 min. The mixture was partitioned between water (50 mL) and CH2Cl2 (125 mL). The organic layer was separated, dried (MgSO4), and concentrated in vacuo to afford 7.32 g (93%) of the title compound: 1H-NMR (CDCl3; 400 MHz): δ 8.12 (d, 2H, J=8.8 Hz), 7.58 (d, 2H, J=8.8 Hz), 5.30 (s, 1H), 4.34-4.28 (m, 1H), 4.26-4.11 (m, 9H), 1.32-1.20 (m, 12H).
References:
US2007/249593,2007,A1 Location in patent:Page/Page column 24
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22399-00-4
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126989-14-8
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