(1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester

Base Information

• Chemical Name: (1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester
• CAS No.: 122346-77-4
• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.273
• Mol file: 122346-77-4.mol

Synonyms:(1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester

Chemical Property of (1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester

There total 1 articles about (1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester 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: 87.0%

(1R,2R)-Essigsaeure-<1,2-epoxy-4,4-(ethylendioxy)-2,6,6-trimethylcyclohexan-1-methyl>ester → (1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester (122346-77-4) + (S)-Essigsaeure-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-methyl)ester

Guidance literature:

With Montmorillonite; water; magnesium sulfate; In toluene; for 0.05h;

DOI:10.1002/hlca.19880710502

Reference yield:

(1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester (122346-77-4) → Violaxanthin (126-29-4)

Guidance literature:

Multi-step reaction with 6 steps

2: oxalyl chloride, (i-Pr)2EtN, DMSO / CH₂Cl₂ / 4 h

3: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature

4: 94 percent / DIBAH, H₂O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature

5: 91 percent / MnO₂ / ethyl acetate / 2.5 h / Ambient temperature

6: methanol / 30 min, -50 deg C, 2 h, -10 deg C, 12 h, r.t.

With methanol; manganese(IV) oxide; oxalyl dichloride; potassium tert-butylate; water; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;

DOI:10.1002/hlca.19880710502

Reference yield:

(1R,2R)-Essigsaeure-(1,2-epoxy-2,6,6-trimethyl-4-oxocyclohexan-1-methyl)ester (122346-77-4) → (15Z)-Violaxanthin (126-29-4,1263-54-3,24502-89-4,24620-97-1,25493-67-8,26917-74-8,26917-75-9,26927-07-1,29246-93-3,75715-58-1,80629-23-8,80629-24-9,101627-32-1,101627-33-2,101627-34-3,101627-35-4,113667-07-5,115182-31-5,116126-19-3,122407-49-2,122407-51-6,147383-89-9,147383-90-2,147383-91-3)

Guidance literature:

Multi-step reaction with 7 steps

2: oxalyl chloride, (i-Pr)2EtN, DMSO / CH₂Cl₂ / 4 h

3: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature

4: 94 percent / DIBAH, H₂O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature

5: 91 percent / MnO₂ / ethyl acetate / 2.5 h / Ambient temperature

6: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature

7: 75 percent / H₂ / Lindlar-catalyst / ethyl acetate / 0.5 h

With methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; n-butyllithium; oxalyl dichloride; potassium tert-butylate; water; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate;

DOI:10.1002/hlca.19880710502

Downstream raw materials:

Violaxanthin

(15Z)-Violaxanthin

(1'S,2'R,4'S,2E,4E)-5-(1',2'-Epoxy-4'-hydroxy-2',6',6'-trimethylcyclohexyl)-3-methyl-2,4-pentadienal