2-Propenoic acid, 3-(4-hydroxy-2-methoxyphenyl)-, (2E)- synthesis
- Product Name:2-Propenoic acid, 3-(4-hydroxy-2-methoxyphenyl)-, (2E)-
- CAS Number:73490-39-8
- Molecular formula:C10H10O4
- Molecular Weight:194.18
141-82-2
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Yield:73490-39-8 55%
Reaction Conditions:
in pyridine at 20 - 60; for 2.7 h;
Steps:
2.1 Example 2 (Compound 2); Step 2-1
4-Hydroxy-2-methoxybenzaldehyde (500 mg, 3.29 mmol) was dissolved in pyridine (8mL). Malonic acid (685 mg, 6.58 mmol) and piperidine (1.63 mL, 16.5 mmol) were added, and the mixture was stirred for 1.5 hours at room temperature and then for 1.2 hours at 60 °C. The reaction solution was poured into ice water and made acidic with 6 mol/L hydrochloric acid. The precipitate that was deposited was collected by filtration and washed with water. The product was dried in vacuo at 50 °C, and (E)-3-(4-hydroxy-2-methoxyphenyl) acrylic acid (353 mg, 55% yield) was obtained. APCI-MS m/z: [M-H]- 193.1H-NMR (CDCl3 + CD3OD) δ (ppm): 3.85 (s, 3H), 6.36 (d, J = 16.0 Hz, 1H), 6.43 (d, J = 1.9 Hz, 1H), 6.44 (dd, J = 1.9, 7.5 Hz, 1H), 7.37 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 16.0 Hz, 1H).
References:
EP1431280,2004,A1 Location in patent:Page 24
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