ChemicalBook CAS DataBase List Tabanone

Tabanone synthesis

7synthesis methods

Product Name:Tabanone
CAS Number:13215-88-8
Molecular formula:C13H18O
Molecular Weight:190.28

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Yield:13215-88-8 52.7%

Reaction Conditions:

Stage #1: 3-methyl-4-(2,6,6-trimethylcyclohex-2-enyl)-but-3-en-2-onewith tert.-butylhydroperoxide;bis(acetylacetonate)oxovanadium in acetone at 30 - 35; for 4 h;
Stage #2: with potassium borohydride in ethanol at 25;

Steps:

1-3 A method for synthesizing megastigmatrienone includes the following steps:

(1) 50.1g of special grade α-isomethyl ionone,1.5g vanadyl acetylacetonateAdd to 208.2g of acetone,Stir and keep at 30-35 ° C,Add t-butyl hydrogen peroxide in a constant temperature reaction for 4h,At the end of the reaction, 1.6 g of sodium thiosulfate was added to quench the reaction.After the acetone was recovered in vacuo, the brine was washed 2 to 3 times.Anhydrous sodium sulfate filtered to remove water;(2) Dissolve the oil in step (1) in 50ml of absolute ethanol, add anhydrous calcium chloride, stir at 25 ° C for 30min, add 5.2g potassium borohydride in two batches, and react at constant temperature for 8-10h;(3) Directly add 1.8g of p-toluenesulfonic acid to the reaction product in step (2), heat to 80-82 ° C and reflux for 4h. After the reaction, place at room temperature to remove solids and recover anhydrous ethanol to obtain 38.2g giant beans Trienone crude oil, GC≥55%;(4) 26.4 g of megastigmatrienone was separated from the crude oil of daemon trienone by column chromatography, GC ≥ 70%, and the total yield was 52.7%.

References:

CN110590522,2019,A Location in patent:Paragraph 0013-0015

14398-35-7 Synthesis