ChemicalBook CAS DataBase List 1(3H)-Isobenzofuranone,3-methyl-(9CI)

1(3H)-Isobenzofuranone,3-methyl-(9CI) synthesis

12synthesis methods

Product Name:1(3H)-Isobenzofuranone,3-methyl-(9CI)
CAS Number:3453-64-3
Molecular formula:C9H8O2
Molecular Weight:148.16

24257-93-0 Synthesis

24257-93-0
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Yield: 94%

Reaction Conditions:

with dirhodium tetraacetate;1,3-bis-(diphenylphosphino)propane;scandium tris(trifluoromethanesulfonate) in 1,4-dioxane;water at 100; for 16 h;

Steps:

2.3 A typical procedure of ketone hydroacylation catalyzed by Rh(II) catalyst (Table. 2, entry 1)
General procedure: 2-Benzoylbenzaldehyde 1a (84.1 mg, 0.4 mmol) was dissolved in dioxane (0.5 mL) and an aqueous solution of Sc(OTf)₃ (4.0 μmol, 0.1 mL of 19.7 mg/mL solution of water) was added. To this mixture, Rh(II)-dppp stock solution (shown in 2.1, 0.6 mL) was added and the mixture was stirred at 100 °C under air for 16 h. After the mixture was diluted with EtOAc, the organic phase was washed with water, dried over Na₂SO₄, and filtered. The solvent was removed in vacuo and the conversion of 1a and the yield of 2a was determined by ¹H NMR analysis with reference to an internal standard (1,1,2,2-tetrachloroethane). The crude product was purified by column chromatography packed with silica gel and small amount of amino silica gel (hexane/acetone = 10:1 to3:1) to afford the pure product 2a (76.7 mg, 92% yield).

References:

Yasukawa, Tomohiro;Kobayashi, Shu [Chemistry Letters,2017,vol. 46,# 1,p. 98 - 100] Location in patent:supporting information