ChemicalBook CAS DataBase List Piperonylic acid

Piperonylic acid synthesis

11synthesis methods

Product Name:Piperonylic acid
CAS Number:94-53-1
Molecular formula:C8H6O4
Molecular Weight:166.13

2635-13-4 Synthesis

2635-13-4
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$5.00/1g

124-38-9
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$214.00/14L

94-53-1
304 suppliers
$6.00/5g

Yield:94-53-1 96%

Reaction Conditions:

Stage #1: carbon dioxidewith 1,2-Bis(diphenylphosphino)benzene;copper(II) acetate monohydrate in 1,4-dioxane at 60; for 0.416667 h;Schlenk technique;
Stage #2: 1,2-(methylenedioxy)-4-bromobenzenewith palladium diacetate;triethylamine;Xantphos in 1,4-dioxane;toluene at 100; for 3 h;Schlenk technique;

Steps:

13 Preparation of benzoic acid

General procedure: In a Schlenk (50 mL) reaction flask with a carbon dioxide balloon attached to a branch tube, add Cu (OAc) 2.H2O (0.0125 mmol), 1,2-bis (diphenylphosphine) benzene (0.018 mmol), and 1,4 -Dioxane (2.0mL), PMHS (2.5mmol) was added under stirring, and then the reaction flask was placed in an oil bath at 60 ° C for 25min to react under carbon dioxide atmosphere, followed by toluene (8mL) and bromobenzene (1.0 mmol), Pd (OAc) 2 (0.03 mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.06 mmol), Et3N (2.5 mmol, 2.5 equiva.), The carbon dioxide was then removed and reacted at 100 ° C until the raw bromobenzene disappeared. After cooling to room temperature, sodium hydroxide solution (1M, 10.0mL) was added, stirred for 10min, and filtered. The solid was washed three times with water, and the filtrate was washed with ethyl acetate ( 2 × 10mL) left after extraction, the aqueous layer was adjusted to pH 1-2 with hydrochloric acid solution (1M), extracted with ethyl acetate (3 × 15mL), dried over anhydrous sodium sulfate,The solvent was removed to give benzoic acid. Yield, 65%.

References:

CN110724047,2020,A Location in patent:Paragraph 0085-0086; 0121-0123; 0176

495-76-1 Synthesis