methyl (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxo-cyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoate

Base Information

• Chemical Name: methyl (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxo-cyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoate
• CAS No.: 90122-64-8
• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.483
• Mol file: 90122-64-8.mol

Synonyms:

Chemical Property of methyl (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxo-cyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxo-cyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoate

There total 17 articles about methyl (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxo-cyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoate 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: 72.0%

methanol (67-56-1) + (E)-3-{(1R,2R)-1,3,3-Trimethyl-2-[2-(2-oxo-cyclohex-3-enyl)-ethyl]-cyclohexyl}-acrylic acid (92830-65-4,110715-77-0) → (E)-3-{(1R,2R)-1,3,3-Trimethyl-2-[2-(2-oxo-cyclohex-3-enyl)-ethyl]-cyclohexyl}-acrylic acid methyl ester (90122-64-8,92935-97-2,97906-41-7,110715-78-1)

Guidance literature:

With sulfuric acid;

DOI:10.1016/S0040-4039(01)91019-6

Reference yield: 72.0%

methanol (67-56-1) + (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxocyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoic acid (92830-65-4,110715-77-0) → methyl (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxo-cyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoate (90122-64-8,92935-97-2,97906-41-7,110715-78-1)

Guidance literature:

With sulfuric acid; for 1h; Ambient temperature;

Reference yield:

4-<2-(2-methoxyphenyl)ethyl>-3,5,5-trimethylcyclohex-2-enone (90122-59-1) → methyl (+/-)-(1'RS,2'RS)-3-<1',3',3'-trimethyl-2'-<2-(2-oxo-cyclohex-3-enyl)ethyl>cyclohexyl>prop-2(E)-enoate (90122-64-8,92935-97-2,97906-41-7,110715-78-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 71 percent / triethylaluminium / tetrahydrofuran / 22 h / Ambient temperature

2: 92 percent / boron trifluoride-diethyl ether / CH₂Cl₂ / 5 h / Ambient temperature

3: 1.) DIBAL; 2.) aq. HCl / 1.) DME, reflux, 2 h; 2.) reflux, 2 h.

4: 60 percent / W₁-Raney nickel / acetone / 0.5 h / Ambient temperature

5: 95 percent / sodium hydride / 1,2-dimethoxy-ethane / 4 h / Heating

6: 1.) DIBAL; 2.) water / 1.) diethyl ether, -78 deg C, 1 h; rt, 1 h; 2.) 0 deg C, 0.5 h.

8: 83 percent / Florisil, PCC / CH₂Cl₂ / 3 h / Ambient temperature

9: 70 percent / sulphamic acid, sodium chlorite / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

10: 72 percent / sulphuric acid / 1 h / Ambient temperature

With hydrogenchloride; sodium chlorite; florisil; W₁-Raney nickel; sulfuric acid; boron trifluoride diethyl etherate; aminosulfonic acid; water; triethylaluminum; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; acetone; tert-butyl alcohol;

upstream raw materials:

methanol

(E)-3-{(1R,2R)-1,3,3-Trimethyl-2-[2-(2-oxo-cyclohex-3-enyl)-ethyl]-cyclohexyl}-acrylic acid

(+/-)-(1RS,2SR)-2-<2-(2-methoxyphenyl)ethyl>-1,3,3-trimethylcyclohexanecarbaldehyde

6-{2-[(1R,2R)-2-((E)-3-Hydroxy-propenyl)-2,6,6-trimethyl-cyclohexyl]-ethyl}-cyclohex-2-enone

Refernces

• 1、 Ihara, Masataka,Toyota, Masahiro,Fukumoto, Keiichiro,Kametani, Tetsuji. "INTRAMOLECULAR DOUBLE MICHAEL REACTION. PART II. SYNTHESIS OF ISOATISIRENE TYPE COMPOUND". . p. 3235 - 3238. Retrieved 2007/10/02.