4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile

Base Information

• Chemical Name: 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile
• CAS No.: 190451-98-0
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.165
• Mol file: 190451-98-0.mol

Synonyms:4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile

Chemical Property of 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile

There total 2 articles about 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile 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: 53.0%

5-hydroxy-5-methyl-3-oxo-7-octenenitrile (190451-91-3) → 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile (190451-98-0)

Guidance literature:

5-hydroxy-5-methyl-3-oxo-7-octenenitrile; With ozone; In dichloromethane; at -78 ℃;

With dimethylsulfide; In dichloromethane; at 20 ℃; for 36h; Inert atmosphere;

DOI:10.15227/orgsyn.078.0254

Reference yield:

3-hydroxy-3-methyl-5-hexenoic acid ethyl ester (113997-03-8) → 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile (190451-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / 1) THF-hexane, -78 deg C, 1 h, 2) THF-hexane, -45 deg C, 2 h

2: 1) ozone, 2) dimethyl sulfide / 1) CH₂Cl₂, -78 deg C, 2) Me₂S, room temp., 15 h

With n-butyllithium; dimethylsulfide; ozone;

DOI:10.1021/jo9822885

Reference yield: 58.0%

methylmagnesium chloride (676-58-4) + tert-butyldimethylsilyl chloride (18162-48-6) + 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile (190451-98-0) → 4-methyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)benzenecarbonitrile + (+/-)-(4S,6R)-4-hydroxy-4,6-dimethyl-2-(1,1,2,2-tetramethyl-1-silapropoxy)cyclohex-1-enecarbonitrile

Guidance literature:

methylmagnesium chloride; 4-hydroxy-4-methyl-2-oxo-6-cyclohexenecarbonitrile; With lithium chloride; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo9909709

upstream raw materials:

5-hydroxy-5-methyl-3-oxo-7-octenenitrile

3-hydroxy-3-methyl-5-hexenoic acid ethyl ester

Downstream raw materials:

2-hydroxy-4-methylbenzonitrile