ChemicalBook CAS DataBase List ACETOXYACETONE

ACETOXYACETONE synthesis

6synthesis methods

Product Name:ACETOXYACETONE
CAS Number:592-20-1
Molecular formula:C5H8O3
Molecular Weight:116.12

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Yield:592-20-1 91%

Reaction Conditions:

in benzene for 2 h;Inert atmosphere;Reflux;regioselective reaction;

Steps:

4.2. General procedure for the cleavage of β-hydroxy ethers
General procedure: To a solution of β-hydroxy ether (1 mmol) in dry benzene (10 mL) was added lead (IV) acetate (1.3 mmol) and the reaction mixture was heated at 50 °C (when aldehydes are obtained) or at reflux (when ketones or acetoxy ethers are formed) for the specified time (monitorized by TLC). Then, the reaction was quenched with 5% Na₂SO₃, extracted with Et₂O, washed with water, brine, dried (Na₂SO₄), and concentrated. The residue was chromatographed on silica gel (hexanes/ether) to give the corresponding α-acetoxy carbonyl or α-acetoxy ether compound.

References:

Alvarez-Manzaneda, Enrique;Chahboun, Rachid;Alvarez, Esteban;Alvarez-Manzaneda, Ramón;Mu?oz, Pedro E.;Jimenez, Fermín;Bouanou, Hanane [Tetrahedron,2011,vol. 67,# 46,p. 8910 - 8917] Location in patent:experimental part

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64-19-7 Synthesis