3-(2-PHENOXYPHENYL)ACRYLIC ACID synthesis
- Product Name:3-(2-PHENOXYPHENYL)ACRYLIC ACID
- CAS Number:95433-16-2
- Molecular formula:C15H12O3
- Molecular Weight:240.25
141-82-2
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19434-34-5
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95433-16-2
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$450.00/1g
Yield:95433-16-2 92%
Reaction Conditions:
with piperidine;pyridine at 120; for 3 h;Knoevenagel Condensation;
Steps:
(ii) Preparation of ortho-, meta- and para-PhO-CA
General procedure: To themixture of the corresponding aldehyde (2.52 g, 12.7 mmol) andmalonic acid (1.99 g, 19.1 mmol), dry pyridine (6.5 ml) and piperidine(0.2 ml) were successively added. The mixture was stirred at120 °C for 3 h, cooled to 10 °C and acidified with HCl (~14 ml) at 1:1ratio with cooling and stirring. After 30 min, the precipitate wasfiltered, washed 3 times with H2O (20 ml) and air dried. The yieldsof o-, m- and p-PhO-CA were 92, 91 and 96%, respectively. (E)-3-(2-Phenoxyphenyl)acrylic acid (ortho-PhO-CA): 1H NMR(400 MHz, DMSO) δ 12.44 (s, 1H), 7.89 (dd, J =7.8, 1.2 Hz, 1H), 7.79(d, J =16.2 Hz, 1H), 7.46-7.35 (m, 3H), 7.21 (t, J =7.5 Hz, 1H), 7.15 (t,J= 7.4 Hz, 1H), 6.98 (d, J =7.8 Hz, 2H), 6.92 (d, J =8.1 Hz, 1H), 6.60(d, J =16.1 Hz, 1H). 13C NMR (101 MHz, DMSO) δ 167.48, 156.73,154.72, 137.50, 131.86, 130.16, 128.57, 125.62, 124.26, 123.54, 120.61, 119.41, 118.06. ESI-HRMS (m/z): Calcd for C15H12O3 [M+H]+241.0859, found 241.0861; calcd [M +NH4]+ 258.1125, found258.1128; calculated [M+Na]+ 263.0679, found 263.0683; calcd[6 M+ K]2+ 740.2212, found 740.2166; calcd [6 M+ K]+1479.4350, found 1479.4278.
References:
Kozlov, Maxim V.;Konduktorov, Konstantin A.;Malikova, Alsu Z.;Kamarova, Kamila A.;Shcherbakova, Anastasia S.;Solyev, Pavel N.;Kochetkov, Sergey N. [European Journal of Medicinal Chemistry,2019,vol. 183,art. no. 111723]
108-86-1
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$10.00/5g
95433-16-2
24 suppliers
$450.00/1g
591-50-4
480 suppliers
$10.00/1g
95433-16-2
24 suppliers
$450.00/1g