3-(1,3-DIOXOLAN-2-YL)BENZOPHENONE synthesis

5synthesis methods

Product Name:3-(1,3-DIOXOLAN-2-YL)BENZOPHENONE
CAS Number:85366-46-7
Molecular formula:C16H14O3
Molecular Weight:254.28

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Yield:85366-46-7 367 mg

Reaction Conditions:

Stage #1: 3-(1,3-dioxolan-2-yl)-phenylbromidewith n-butyllithium in tetrahydrofuran at -70; for 1 h;
Stage #2: N-methoxy-N-methylbenzamide in tetrahydrofuran at -70; for 2 h;

Steps:

3 Example 3

The preparation method is as follows:Ethylene glycol acetal (458 mg, 2 mmol) of 3-bromobenzaldehyde,Dissolved in 5 mL of dry tetrahydrofuran,N-Butyllithium (0.8 mL, 2 mmol) was slowly added dropwise at -70 ° C,After 1 hour, N-methyl-N-methoxybenzamide (280 mg, 1.7 mmol) was added slowly at -70 ° C,The reaction was continued at -70 ° C for 2 hours,Add 5mL saturated brine to quench the reaction,The organic phase was extracted with ethyl acetate (10 mL * 3)The combined organic phases are dried over anhydrous sodium sulphate.Spin the solvent,Column chromatography (petroleum ether: ethyl acetate = 20: 1 as eluant),The reaction product 367mg.The reaction product was dissolved in 5 mL of dry methanol,1mL 6N hydrochloric acid was added at room temperature, the reaction 1 hour, the reaction was quenched by adding saturated sodium bicarbonate solution,The organic phase was extracted with ethyl acetate (10 mL * 3). The organic phases were combined and dried over anhydrous sodium sulfate.The solvent was spin-dried and separated by column chromatography (petroleum ether: ethyl acetate = 20: 1 as eluant)The reaction product3-benzoylbenzaldehyde 266 mg, 75% over two steps.

References:

CN107286137,2017,A Location in patent:Paragraph 0097; 0098; 0099; 0100

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100-52-7 Synthesis