ChemicalBook CAS DataBase List 4',4',6,6-Tetramethyl-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione

4',4',6,6-Tetramethyl-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione synthesis

6synthesis methods

Product Name:4',4',6,6-Tetramethyl-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione
CAS Number:1984-51-6
Molecular formula:C17H22O4
Molecular Weight:290.35

2,2'-methanediylbis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

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4',4',6,6-Tetramethyl-3,5,6,7-tetrahydrospiro[benzofuran-2(4H),1'-cyclohexane]-2',4,6'-trione

1984-51-6
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Yield:1984-51-6 69%

Reaction Conditions:

with manganese(III) triacetate dihydrate in acetic acid; for 0.0333333 h;Reflux;

Steps:

4.3. Reaction of methylenebis(cyclohexanedione)s 1a-q in AcOH

General procedure: Methylenebis(cyclohexanedione) 1 (0.5 mmol) in AcOH (10 mL) was heated at 110 °C to dissolve 1, and Mn(OAc)₃*2H₂O (1.25 mmol) was added. The mixture was heated under reflux until the Mn(III) oxidant was completely consumed and the brown color of Mn(III) turned transparent. The existence of the Mn(III) was monitored by iodine-starch paper and each reaction time is listed in Table 1. After completion of the reaction, 2M HCl (10 mL) was added and the aqueous mixture was extracted with CHCl₃ (10 mL * 5). The combined extracts were washed with water (10 mL), a saturated aqueous solution of NaHCO₃ (10 mL), brine (10 mL), dried over anhydrous MgSO₄ (3 g), then concentrated to dryness. The residue was separated by column chromatography on silica gel eluting with 10% EtOAc/CHCl₃, mainly giving the corresponding spiro dihydrofuran 2 together with a small amount of isomeric spiro dihydrofuran 3 and dispiro cyclopropane 4 in some cases (see Table 1).

References:

Hisano, Kazuki;Nishikawa, Satomi;Nishino, Hiroshi;Shibuya, Keisuke;Yokote, Suzuka [Tetrahedron,2020,vol. 76,# 20]

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