ChemicalBook CAS DataBase List CHEMBRDG-BB 5873913

CHEMBRDG-BB 5873913 synthesis

5synthesis methods

Product Name:CHEMBRDG-BB 5873913
CAS Number:6093-74-9
Molecular formula:C13H12O5
Molecular Weight:248.23

106-94-5 Synthesis

106-94-5
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105-53-3
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95-01-2
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6093-74-9
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$133.00/5G

Yield:6093-74-9 98.1%

Reaction Conditions:

Stage #1: diethyl malonate;2,4-Dihydroxybenzaldehydewith piperidine;acetic acid in ethanol; for 30 h;Reflux;
Stage #2: propyl bromidewith potassium carbonate in N,N-dimethyl-formamide at 20; for 48 h;
Stage #3: with ethanol;sodium hydroxide in N,N-dimethyl-formamide; for 0.25 h;Reflux;

Steps:

19

Add 2,4-dihydroxybenzaldehyde (2.76g, 20mmol), diethyl malonate (3.84g, 24mmol), piperidine (0.2mL), 2 drops of acetic acid, ethanol (24mL) into a 100mL single-necked flask, The reaction was refluxed for 30 hours. After the reaction was completed, it was cooled and poured into 40 mL of ice water to precipitate a solid, filtered, washed with 50% ice ethanol, and recrystallized with 50% ice ethanol to obtain a yellow solid (3.53 g) with a yield of 75.5%.The yellow solid (2.34g, 10mmol), potassium carbonate (1.66g, 12mmol), DMF (25mL) were added to a 100mL single-neck flask, bromopropane (1.85g, 15mmol) was added dropwise, and the reaction was carried out at room temperature for 48h.After the reaction, 30 mL of water was added to precipitate a solid, which was filtered and dried to obtain a white solid (2.72 g) with a yield of 98.4%.Add the above white solid (2.76g, 10mmol), 10% sodium hydroxide (15mL), ethanol (15mL) to a 100mL single-necked flask, and reflux for 15min. After the reaction, add hydrochloric acid dropwise to adjust pH 2, precipitate solids, and filter. After washing with water and drying, a white solid 3-carboxy-7-propoxycoumarin (2.43g) was obtained with a yield of 98.1%.

References:

CN110804045,2020,A Location in patent:Paragraph 0270; 0274-0276