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CAS No. : | 2373-80-0 | MDL No. : | MFCD00005837 |
Formula : | C10H8O4 | Boiling Point : | No data available |
Linear Structure Formula : | C6H3CH2CH2COOCO2H | InChI Key : | QFQYZMGOKIROEC-DUXPYHPUSA-N |
M.W : | 192.17 | Pubchem ID : | 643181 |
Synonyms : |
|
Chemical Name : | 3-(Benzo[d][1,3]dioxol-5-yl)acrylic acid |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 20℃; for 22h; | To a solution of (3,4-methylenedioxy)-cinnamic acid (1 .5g, 7.8 mmol) in MeOH (200mL), acetic acid (10 mL) was added 10% Pd/C (500 mg) under N2 atmosphere. The mixture was stirred at room temperature for 22 hours under H2 atmosphere. Then the mixture was filtered through celite and washed with MeOH (200 mL). The filtrate was concentrated to give compound IntA-Q-12-1 as off-white crystalline solid (1.51 g, 99%).‘H NIVIR (400 MHz, CDC13) 5 6.74 - 6.64 (m, 3H), 5.92 (s, 2H), 2.87 (t, J= 7.8 Hz, 2H),2.63 (t, J 7.2 Hz, 2H). |
80% | Pd-C; In ethanol; | 7.1 Synthesis of 3-benzo-1,3-dioxol-5-ylpropionic acid 3-benzo-1,3-dioxol-5-ylacrylic acid (2 g) was hydrogenated in ethanol (50 ml) over 5% Pd-C under a pressure of hydrogen at 10 psi for 40 mins to give 3-benzo-1,3-dioxol-5-ylpropionic acid (1.67 g, 80% yield) as a solid, m.p. 86.1-88.3 C. (Lit m.p. 87-88 C.)10 |
80% | Pd-C; In ethanol; | 7.1 Synthesis of 3-benzo-1,3-dioxol-5-ylpropionic Acid 3-benzo-1,3-dioxol-5-ylacrylic acid (2 g) was hydrogenated in ethanol (50 ml) over 5% Pd-C under a pressure of hydrogen at 10 psi for 40 mins to give 3-benzo-1,3-dioxol-5-ylpropionic acid (1.67 g, 80% yield) as a solid, m.p. 86.1-88.3 C. (Lit m.p. 87-88 C.)10. |
80% | Pd-C; In ethanol; | 7.1 Synthesis of 3-benzo-1,3-dioxol-5-ylpropionic Acid 3-benzo-1,3-dioxol-5-ylacrylic acid (2 g) was hydrogenated in ethanol (50 ml) over 5% Pd-C under a pressure of hydrogen at 10 psi for 40 mins to give 3-benzo-1,3-dioxol-5-ylpropionic acid (1.67 g, 80% yield) as a solid, m.p. 86.1-88.3 C. (Lit m.p. 87-88 C.)10 |
palladium-carbon; In methanol; hydrogen; | SYNTHESIS EXAMPLE 41 Synthesis of 3-(3,4-methylenedioxy-phenyl)-propionic acid In 5 ml of absolute methanol was dissolved 500 mg of 3,4-methylenedioxy-cinnamic acid, followed by adding thereto 50 mg of 10% palladium-carbon, and the reaction was carried out with stirring in a hydrogen stream at room temperature for 5 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was recrystallized from methanol to obtain 285 mg of the desired compound. NMR; (60 MHz, δ values in CDCl3), 2.71 (4H, --CH2 --CH2 --), 5.82 (2H, s, --O--CH2 --O--), 6.57 (3H, aromatic proton). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 16h; | 10% Pd/C (1.2 g, 10 mol%) was placed in a 250 ml round-bottomed flask and the balloon replaced with hydrogen gas three times. After the hot ethanolDissolved compound 2b (12.0 g, 62.4 mmol) was added to the above reaction flask and stirred at room temperature for 16 hours. The reaction was monitored by TLC until the compound 2b reaction was complete. The reaction solution was filtered through celite, and the filtrate was evaporated to dryness under reduced pressure to remove the ethanol solvent to give an off-white solid 3b (m.p.=82-84C). The next reaction without further purification gave a crude yield of 74.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 30℃; for 8h; | To a solution of (E)-3-(benzo[d][ l,3]dioxol-5-yl)acrylic acid (5), (300 mg, 1.56 mmol) in dry DCM, EDC.HC1 (315 mg, 2.0 mmol), HOBt (274 mg, 2.0 mmol) and ' diisopropylethylamine (0.8 mL, 4.7 mmol) was added at 0 C. Then the silapiperidine salt, 2 (285 mg, 1.7 mmol) was added and stirred at RT (30C) for' 8 h. The reaction was quenched by the addition of water and the organic layer was separated, washed with saturated NaHC03, IN HC1, dried over Na2S04 and concentrated under reduced pressure. This crude mixture was purified by column chromatography using pet ether- ethyl acetate (70:30) to give the title compound (360 mg, 77 % yield) as a crystalline white solid. H NMR (400 MHz, CDCI3) : delta 7.61 (d, J = 15.3 Hz, 1H), 7.05 (s, 1H), 7.01 (d, J= 8.0 Hz, 1H), 6.81-6.73 (m, 2H), 5.99 (s, 2H), 3.81 (t, J =6.3 Hz, 2H), 3.75 (t, J = 6.3 Hz, 2H), 0.90-0.83 (m, 4H), 0.12 (s, 6H); 13C NMR (100 MHz, CDC13): delta 165.5, 148.8, 148.1, 142.2, 129.9, 123.6, 1 15.5, 108.4, 106.3, 101.4, 45.5, 42.8, 15.6, 13.8, -3.0 (2C). |
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