4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione

Base Information

• Chemical Name: 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione
• CAS No.: 118966-45-3
• Molecular Formula: C₂₄H₂₈O₄
• Molecular Weight: 380.484

Synonyms:4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione

Chemical Property of 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione

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Technology Process of 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione

There total 6 articles about 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(4-methylphenyl)methyl]-5,5-dimethylcyclohex-2-en-1-one (139484-11-0) → 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione (118966-45-3)

Guidance literature:

With manganese(III) triacetate dihydrate; In formic acid; acetic acid; at 20 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1016/j.tet.2020.131165

Reference yield: 82.0%

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine (35024-12-5) + 4-methyl-benzaldehyde (104-87-0) + dimedone (126-81-8) → 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione (118966-45-3)

Guidance literature:

With potassium hydroxide; In 1,4-dioxane; at 110 ℃; for 0.3h; regioselective reaction; Microwave irradiation;

DOI:10.1002/jhet.1732

Reference yield: 71.0%

3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(4-methylphenyl)methyl]-5,5-dimethylcyclohex-2-en-1-one (139484-11-0) → 4’,4’,6,6-tetramethyl-3-(p-tolyl)-6,7-dihydro-3H-spiro[benzofuran-2,1’-cyclohexane]-2’,4,6’(5H)-trione (118966-45-3) + 4',4',6,6-tetramethyl-2-(p-tolyl)-6,7-dihydro-2H-spiro[benzofuran-3,1'-cyclohexane]-2',4,6'(5H)-trione (118966-44-2)

Guidance literature:

With manganese(III) triacetate dihydrate; In acetic acid; for 0.0333333h; Reflux;

DOI:10.1016/j.tet.2020.131165

upstream raw materials:

4-methyl-benzaldehyde

triphenylbismuthonio-4,4-dimethyl-2,6-dioxocyclohexane-1-ide

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine

dimedone

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