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

Base Information

• Chemical Name: 3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid
• CAS No.: 374782-77-1
• Molecular Formula: C₁₃H₂₂O₂
• Molecular Weight: 210.316
• Mol file: 374782-77-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about 3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid 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: 91.0%

(+)-methyl 3-[(1R)-1,3,3-trimethyl-2-methylenecyclohexyl]propionate (374782-78-2) → 3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid (374782-77-1)

Guidance literature:

With sodium hydroxide; In methanol; for 12h; Heating;

DOI:10.1021/jo0105484

Reference yield:

(+)-(5S)-5-isopropenyl-2,6,6-trimethylcyclohex-2-enone (179259-37-1) → 3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid (374782-77-1)

Guidance literature:

Multi-step reaction with 14 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

14: 91 percent / aq. NaOH / methanol / 12 h / Heating

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) → 3-((R)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionic acid (374782-77-1)

Guidance literature:

Multi-step reaction with 8 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

8: 91 percent / aq. NaOH / methanol / 12 h / Heating

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:

3-((S)-1,3,3-Trimethyl-2-methylene-cyclohexyl)-propionaldehyde

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

(+)-(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