ChemicalBook CAS DataBase List 4-METHOXYCINNAMIC ACID

4-METHOXYCINNAMIC ACID synthesis

12synthesis methods

Product Name:4-METHOXYCINNAMIC ACID
CAS Number:943-89-5
Molecular formula:C10H10O3
Molecular Weight:178.18

4-methoxycinnamic acid synthesis : In a 25-mL, roundbottomed flask, 4-methoxybenzaldehyde (0.804 mL, 6.61 mmol) (3), malonic acid (1.75 g, 16.8 mmol), and β-alanine (0.10 g, 1.12 mmol) were dissolved in pyridine (3.0 mL, 37.1 mmol) and heated under reflux for 90 minutes. After cooling to room temperature, the reaction mixture was placed in an ice bath and 8.0 mL of concentrated HCl was slowly added. The resulting white precipitate was collected by vacuum filtration, washed with cold water (2 x 10mL) and dried thoroughly. The product was recrystallized from absolute ethanol (~20 mL).

Synthesis of 4-methoxycinnamic acid

141-82-2 Synthesis

141-82-2
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$5.00/25g

123-11-5 Synthesis

123-11-5
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$10.00/10g

943-89-5
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$19.89/10g

Yield:943-89-5 98%

Reaction Conditions:

with piperidine in pyridine for 4 h;Reflux;

Steps:

Synthesis of (E)-3-(4-Methoxyphenyl)acrylic acid (7b)
Malonic acid (1.24 g, 12 mmol) was added to a stirred solution of 6b (1.36 g, 10 mmol), pyridine(6 mL) and piperidine (0.6 mL). The reaction was stirred at reflux for 4 h. The mixture was then cooledto room temperature and poured into a solution of HCl (10 M in H2O, 80 mL) at 0 °C. The white solidthat formed was recovered by filtration and washed with water (200 mL) to afford the title compoundas white powder (1.33g, 98%). 1H NMR (300 MHz, CD3OD) δ 7.62 (d, J = 16.0 Hz, 1H), 7.58-7.47 (m,2H), 7.01-6.88 (m, 2H), 6.33 (d, J = 15.9 Hz, 1H), 3.82 (s, 3H). Data were in accordance with theliterature [28].

References:

Cornelio, Marinonio L.;Jones, Alan M.;Le Duff, Cécile S.;Povinelli, Ana Paula R.;Tang, Bridget;Zazeri, Gabriel [Molecules,2020,vol. 25,# 12]

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104-92-7 Synthesis