ChemicalBook CAS DataBase List (E)-2,4,4-trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one

(E)-2,4,4-trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one synthesis

7synthesis methods

Product Name:(E)-2,4,4-trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one
CAS Number:29790-29-2
Molecular formula:C13H18O2
Molecular Weight:206.2808

79-77-6 Synthesis

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(E)-2,4,4-trimethyl-3-(3-oxo-1-butenyl)cyclohex-2-en-1-one

29790-29-2
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Yield:29790-29-2 75%

Reaction Conditions:

with sodium bromate;sodium hydrogen sulfate;potassium iodide in dichloromethane;water at 35 - 40; for 6.5 h;

Steps:

2

Example 2; 4-oxo-β-ionone 5 IInto a suitable reaction vessel, under an atmosphere of nitrogen, is loaded 100 g of 4-oxo-β-ionone (520 mmol) and 500 mL of methylene chloride; the reaction mixture is heated at 37°C and in the meantime a solution containing 9.6 g of potassium iodide (58 mmol) dissolved in 60 mL of water added, followed by a solution containing 17 g of sodium bisulphate monohydrate (123 mmol) dissolved in 35 mL of water. A solution containing 79.2 g of sodium bromate (525 v rnmol) , dissolved in 250 mL of water, is added dropwise at 35-40⁰C over as period of 2.5 hours. The reaction mix is stirred at 35-40⁰C for 4 hours and the progress of the reaction monitored by GC/HPLC. Upon completion of the reaction, the system is cooled to 25⁰C, the acidic aqueous phase separated and the organic phase treated with a solution containing 31 g of sodium hydroxide in 200 mL of water, then with a solution of 15.6 g of sodium hydroxide in 100. mL of water, then with a solution containing 15.0 mL of acetic acid and 1.5 g of sodium bisulphite in 100 mL of water and finally with 100 mL of water. The organic phase is treated with 10 g of acticarbone, filtered, and then concentrated to a residue under vacuum. 400 mL of heptane isomer mixture are added and the suspension heated to 35-40⁰C, then cooled to 0⁰C: the 4-oxo-β- ionone precipitate is then filtered, washed with 80 mL of heptane and then dried to constant weight under vacuum at 25-30⁰C, to give 80.5 g of 4-oxo-β-Ionone (75%) with purity (as judged by HPLC) > 97%.

References:

WO2007/72529,2007,A2 Location in patent:Page/Page column 21-22

79-77-6 Synthesis

79-77-6
245 suppliers
$10.00/25g

29790-29-2
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inquiry

14398-34-6 Synthesis