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ChemicalBook CAS DataBase List Watermelon Ketone

Watermelon Ketone synthesis

3synthesis methods
The material is prepared by etherification of 4-methylpyrocatechol with two equivalents of alkyl 2-bromoacetate and subsequentDieckmann condensation followed by hydrolysis and decarboxylation.
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Yield:28940-11-6 95%

Reaction Conditions:

with 2-iodobenzenesulfonic acid in nitromethane at 25; for 6.5 h;Solvent;Reagent/catalyst;

Steps:

2-7 Example 6: Synthesis of watermelonone with o-iodobenzenesulfonic acid oxidant

The reaction vessel is a 500 mL four-necked flask with a thermometer, a magnetic stirrer, a reflux condenser and a constant pressure dropping funnel.The calone precursor alcohol (2.980 g, 16.7 mmol) prepared in Example 1 was dissolved in 40 mL of dry nitromethane, and added to 70 mL of nitromethane (dissolved with 7.110 g, 25.05 mmol) at room temperature (25° C.). , 1.5eqv of o-iodobenzenesulfonic acid), after stirring the reaction for 6.5h, 120mL of ethyl acetate was added to the reaction mixture to obtain a white suspension, the white solid was filtered out, the organic layer was washed once with water, and the solvent was evaporated by rotary evaporation. , 2.88 g of crude calone was obtained, and 2.86 g of finished calone was obtained through recrystallization, with a yield of 95.0% and a purity of 99.1% (gas chromatography).

References:

CN113651795,2021,A Location in patent:Paragraph 0034-0059

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