ChemicalBook CAS DataBase List 8-METHYLFLAVONE

8-METHYLFLAVONE synthesis

8synthesis methods

Product Name:8-METHYLFLAVONE
CAS Number:70794-01-3
Molecular formula:C16H12O2
Molecular Weight:236.27

824-42-0
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2-(Dimethyl (oxo)-λ6-sulfanylidene)-1-phenylethan-1-one

20718-17-6
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70794-01-3
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Yield:70794-01-3 89%

Reaction Conditions:

Stage #1: 2-methoxy-3-methylbenzaldehyde;2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-onewith dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer;cesium acetate in 1,2-dichloro-ethane at 100; for 6 h;Sealed tube;Inert atmosphere;
Stage #2: with sulfuric acid;acetic acid in 1,2-dichloro-ethane at 100; for 3 h;Sealed tube;Inert atmosphere;

Steps:

General procedure for the synthesis of 3

General procedure: A sealed tube was charged with 1a (0.2 mmol, 1.0 equiv.), 2a (0.3 mmol, 1.5 equiv.), [Cp*RhCl₂]₂ (0.005 mmol, 2.5 mol%), and CsOAc (0.1 mmol, 0.5 equiv.) in DCE (2 mL). After the reaction mixture had been stirred at 100 °C under Ar for 6 h, 1 mL of H₂SO₄/HOAc (10 μL of H₂SO₄dissolved in 0.99 mL of HOAc) was added at room temperature. After completion of the addition, the reaction mixture was then stirred at 100 °C for 3 h before being cooled to room temperature. The mixture was diluted with EtOAc (20 mL), washed with brine, and dried over anhydrous Na₂SO₄. After removal of the EtOAc, the residue was purified by chromatography on basic silica gel (PE/EtOAc = 8/1) to afford 3aa (40 mg, 89%) as a white solid.

References:

Cheng, Kang;Chen, Jinkang;Jin, Licheng;Zhou, Jian;Jiang, Xinpeng;Yu, Chuanming [Journal of Chemical Research,2019,vol. 43,# 9-10,p. 392 - 398]