Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate

Base Information

• Chemical Name: Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate
• CAS No.: 62096-98-4
• Molecular Formula: C₁₆H₂₂O₃
• Molecular Weight: 262.349

Synonyms:Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate

Chemical Property of Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate

There total 18 articles about Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate 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:

2,5-dimethylcyclohexanone (932-51-4) → Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate (62096-98-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) 1,2-dimethoxyethane , Ethanol heat for 14.5 h; 2.) 15 min,0 deg C

2: 1.) O₃; 2.) Zn,50percentHOAc / 1.) CH₂Cl₂,- 78 deg C; 2.) reflux

3: 79 percent / Jones reagent / acetone

4: 95 percent / K₂CO₃ / acetone / 2 h / Heating

5: 97 percent / Br₂ / acetic acid; acetic acid / 6.5 h

6: 91 percent / CaCO₃ / N,N-dimethyl-acetamide / 0.75 h / Heating

7: 95 percent / KOH / H₂O; ethanol / 15.5 h / Ambient temperature

8: 1.) Diisobutylaluminum hydride; 2.) 20percentH₂SO₄ / 1.) CH₂Cl₂, 0 deg C,benzene,15 min.; 45 min.at room temp.,2.) 30 min., 0 deg C

9: LDA

10: LDA

11: 100 percent / NaIO₄ / OsO₄ / H₂O; 2-methyl-propan-2-ol / 30 h / Ambient temperature

12: 85 percent / Jones reagent / acetone

13: diethyl ether

14: 1.) NaNH₂,bis(trimethylsilyl)amine

15: 1.) HCl; 2.) 2,4,5-collidine / 1.) CH₂Cl₂,-20 deg C; 2.) 180-185 deg C, 25 min.

With 2,4,5-trimethylpyridine; hydrogenchloride; potassium hydroxide; sodium periodate; jones reagent; sulfuric acid; bromine; diisobutylaluminium hydride; potassium carbonate; ozone; sodium amide; acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; zinc; lithium diisopropyl amide; osmium(VIII) oxide; In diethyl ether; ethanol; N,N-dimethyl acetamide; water; acetic acid; acetone; tert-butyl alcohol;

DOI:10.1021/jo01309a003

Reference yield:

(1,4-Dimethyl-2-oxo-cyclohexyl)-acetaldehyde (74592-60-2) → Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate (62096-98-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 79 percent / Jones reagent / acetone

2: 95 percent / K₂CO₃ / acetone / 2 h / Heating

3: 97 percent / Br₂ / acetic acid; acetic acid / 6.5 h

4: 91 percent / CaCO₃ / N,N-dimethyl-acetamide / 0.75 h / Heating

5: 95 percent / KOH / H₂O; ethanol / 15.5 h / Ambient temperature

6: 1.) Diisobutylaluminum hydride; 2.) 20percentH₂SO₄ / 1.) CH₂Cl₂, 0 deg C,benzene,15 min.; 45 min.at room temp.,2.) 30 min., 0 deg C

7: LDA

8: LDA

9: 100 percent / NaIO₄ / OsO₄ / H₂O; 2-methyl-propan-2-ol / 30 h / Ambient temperature

10: 85 percent / Jones reagent / acetone

11: diethyl ether

12: 1.) NaNH₂,bis(trimethylsilyl)amine

13: 1.) HCl; 2.) 2,4,5-collidine / 1.) CH₂Cl₂,-20 deg C; 2.) 180-185 deg C, 25 min.

With 2,4,5-trimethylpyridine; hydrogenchloride; potassium hydroxide; sodium periodate; jones reagent; sulfuric acid; bromine; diisobutylaluminium hydride; potassium carbonate; sodium amide; 1,1,1,3,3,3-hexamethyl-disilazane; calcium carbonate; lithium diisopropyl amide; osmium(VIII) oxide; In diethyl ether; ethanol; N,N-dimethyl acetamide; water; acetic acid; acetone; tert-butyl alcohol;

DOI:10.1021/jo01309a003

Reference yield:

(3a-cis)-3a,4,5,7a-Tetrahydro-3a,6-dimethyl-2(3H)-benzofuranone (33722-72-4) → Methyl 3-Methyl-3-(1-methyl-4-methylene-2-cyclohexenyl)-2-oxocyclopentanecarboxylate (62096-98-4)

Guidance literature:

Multi-step reaction with 7 steps

1: LDA

2: LDA

3: 100 percent / NaIO₄ / OsO₄ / H₂O; 2-methyl-propan-2-ol / 30 h / Ambient temperature

4: 85 percent / Jones reagent / acetone

5: diethyl ether

6: 1.) NaNH₂,bis(trimethylsilyl)amine

7: 1.) HCl; 2.) 2,4,5-collidine / 1.) CH₂Cl₂,-20 deg C; 2.) 180-185 deg C, 25 min.

With 2,4,5-trimethylpyridine; hydrogenchloride; sodium periodate; jones reagent; sodium amide; 1,1,1,3,3,3-hexamethyl-disilazane; lithium diisopropyl amide; osmium(VIII) oxide; In diethyl ether; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo01309a003

upstream raw materials:

Methyl(3α,3aα,7aα)-2,3,3a,4,5,7a-Hexahydro-3,3a,6-trimethyl-2-oxo-3-benzofuranbutanoate

Methyl((1α,2α)-2-Hydroxy-1,4-dimethyl-3-cyclohexen-1-yl)-3-methyl-2-oxocyclopentanecarboxylate

2,5-dimethylcyclohexanone

(3a-cis)-3a,4,5,7a-Tetrahydro-3a,6-dimethyl-2(3H)-benzofuranone

Downstream raw materials:

(+/-)-trichodiene

(2RS,1'SR)-2-(1',4'-dimethylcyclohex-3'-enyl)-2-methylcyclopentan-1-one

2-Methyl-2-(1-methyl-4-methylenecyclohex-1-yl)cyclopentanone

2-Methyl-2-(1-methyl-4-methylene-2-cyclohexen-1-yl)-cyclopentanol

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