3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid

Base Information

• Chemical Name: 3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid
• CAS No.: 76184-66-2
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• Mol file: 76184-66-2.mol

Synonyms:3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid

Chemical Property of 3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid

There total 2 articles about 3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-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:

2-(2,6-Dimethyl-4-oxo-cyclohex-2-enylmethyl)-malonic acid diethyl ester (76184-65-1) → 3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid (76184-66-2)

Guidance literature:

With hydrogenchloride; for 20h; Heating;

Reference yield:

→ 3-((1S,6R)-2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid (76184-66-2)

Guidance literature:

Dienon (4) 1. Na-malonat, HCl (N), CH2N2 2. Hydrolyse;

DOI:10.1139/v70-550

Reference yield:

3-(2,6-Dimethyl-4-oxo-cyclohex-2-enyl)-propionic acid (76184-66-2) → (±)-agarospirol (1460-73-7,19890-17-6,19890-18-7,23811-08-7,59331-07-6,59331-08-7,66537-53-9,121840-72-0,26934-83-8,4895-33-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 22 g / diethyl ether

2: 72 percent / p-toluenesulfonic acid / benzene / 40 h / Heating

3: 6 g / potassium hydroxide, water / 3 h / Heating

4: oxalyl chloride, pyridine / benzene / 2 h / Ambient temperature

5: 1.5 g / diethyl ether

6: copper / benzene / 3.5 h / Heating

7: 11.85 g / sodium hydride / 10.5 h / Heating

8: 3.47 g / sodium borohydride / methanol / 3 h / 0 °C

9: 82 percent / 1 N hydrochloric acid / tetrahydrofuran / 4 h / Heating

10: 90 percent / diethyl ether; CH₂Cl₂ / 0.17 h / Ambient temperature

11: 62 percent / lithium tri-tert-butoxyaluminium hydride / diethyl ether / 4 h / Ambient temperature

12: 1.) magnesium / 1.) ether, 2.) ether, reflux, 2 h

13: 91 percent / pyridine / 3 h / Ambient temperature; in the dark

14: 92 percent / lithium, ethylamine / diethyl ether / 2.5 h

With pyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; oxalyl dichloride; lithium tri(t-butoxy)aluminum hydride; water; lithium; copper; sodium hydride; toluene-4-sulfonic acid; magnesium; ethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

upstream raw materials:

2-(2,6-Dimethyl-4-oxo-cyclohex-2-enylmethyl)-malonic acid diethyl ester

Downstream raw materials:

(±)-agarospirol

N-[(5S,10S)-6,10-Dimethyl-spiro[4.5]dec-6-en-(2Z)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine

N-[(5S,10R)-6,10-Dimethyl-spiro[4.5]dec-6-en-(2E)-ylidene]-N'-(2,4-dinitro-phenyl)-hydrazine