(+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate

Base Information

• Chemical Name: (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate
• CAS No.: 374782-78-2
• Molecular Formula: C₁₄H₂₄O₂
• Molecular Weight: 224.343
• Mol file: 374782-78-2.mol

Synonyms:(+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate

Chemical Property of (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate

There total 16 articles about (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate 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: 78.0%

methanol (67-56-1) + 1-Diazo-3-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-propan-2-one (374782-83-9) → (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate (374782-78-2)

Guidance literature:

for 1h; Photolysis;

DOI:10.1021/jo0105484

Reference yield:

(+)-(5S)-5-isopropenyl-2,6,6-trimethylcyclohex-2-enone (179259-37-1) → (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate (374782-78-2)

Guidance literature:

Multi-step reaction with 13 steps

1: diethyl ether / 0 - 20 °C

2: 750 mg / PCC; silica gel / CH₂Cl₂ / 12 h

3: 90 percent / NBS / CH₂Cl₂; methanol / 6 h / 0 - 5 °C

4: 76 percent / potassium tert-butoxide / tetrahydrofuran / -5 - 20 °C

5: O₃; NaHCO₃ / CH₂Cl₂ / 0.08 h / -70 °C

6: 93 mg / Ac₂O; Et₃N; 4-N,N-(dimethylamino)pyridine / benzene / 6 h / Heating

7: 90 percent / H₂ / Pd/C / ethyl acetate / 0.5 h

8: 60 percent Turnov_. / BF₃*OEt₂ / benzene / 2 h / 0 - 5 °C

9: 90 percent / Raney Ni / ethanol / 0.5 h / Heating

10: 94 percent / aq. NaOH / methanol / 12 h / Heating

11: oxalyl chloride / benzene / 2 h / 20 °C

12: 22 mg / diethyl ether / 2 h / 20 °C

13: 78 percent / 1 h / Photolysis

With dmap; sodium hydroxide; N-Bromosuccinimide; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; acetic anhydride; silica gel; nickel; sodium hydrogencarbonate; ozone; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; benzene; 6: Criegee rearrangement / 13: Wolff rearrangement;

DOI:10.1021/jo0105484

Reference yield:

(+)-methyl (1R)-1,5,5-trimethyl-6-methylenecyclohex-3-en-2-one-1-acetate (302840-41-1) → (+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate (374782-78-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / H₂ / Pd/C / ethyl acetate / 0.5 h

2: 60 percent Turnov_. / BF₃*OEt₂ / benzene / 2 h / 0 - 5 °C

3: 90 percent / Raney Ni / ethanol / 0.5 h / Heating

4: 94 percent / aq. NaOH / methanol / 12 h / Heating

5: oxalyl chloride / benzene / 2 h / 20 °C

6: 22 mg / diethyl ether / 2 h / 20 °C

7: 78 percent / 1 h / Photolysis

With sodium hydroxide; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; nickel; palladium on activated charcoal; In methanol; diethyl ether; ethanol; ethyl acetate; benzene; 7: Wolff rearrangement;

DOI:10.1021/jo0105484

upstream raw materials:

methanol

1-Diazo-3-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-propan-2-one

(+)-(5S)-5-isopropenyl-2,6,6-trimethylcyclohex-2-enone

(+)-(5S)-5-isopropenyl-2,3,4,4-tetramethylcyclohex-2-en-1-one

Downstream raw materials:

1-Diazo-4-((R)-1,3,3-trimethyl-2-methylene-cyclohexyl)-butan-2-one

3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid