(2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal

Base Information

• Chemical Name: (2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal
• CAS No.: 130815-76-8
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 130815-76-8.mol

Synonyms:

Chemical Property of (2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal

There total 7 articles about (2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal 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:

(E)-4-(1',6'-Epoxy-2',2',6'-trimethyl-4'-cyclohexen-1'-yl)-3-buten-2-on (30981-78-3,54685-98-2,75222-70-7,80924-22-7) → (2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal (130815-76-8,130856-71-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 52 percent / conc. H₂SO₄ / acetic acid; diethyl ether / 2 h / 0 °C

2: 6.6 g / KOH / methanol / 2 h / Ambient temperature

3: 3.16 g / TsOH / CH₂Cl₂ / 4 h

4: 1.2 g

5: 0.80 g / DIBAH / hexane; diethyl ether / 0 °C

6: 295 g / MnO₂ / ethyl acetate / 1.5 h

7: 52 mg / aq. AcOH / Ambient temperature

With manganese(IV) oxide; potassium hydroxide; diisobutylaluminium hydride; acetic acid; sulfuric acid; toluene-4-sulfonic acid; In methanol; diethyl ether; hexane; dichloromethane; acetic acid; ethyl acetate;

DOI:10.1002/hlca.19900730426

Reference yield:

Acetic acid 6-acetoxy-2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester (130815-69-9,130856-72-3) → (2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal (130815-76-8,130856-71-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 6.6 g / KOH / methanol / 2 h / Ambient temperature

2: 3.16 g / TsOH / CH₂Cl₂ / 4 h

3: 1.2 g

4: 0.80 g / DIBAH / hexane; diethyl ether / 0 °C

5: 295 g / MnO₂ / ethyl acetate / 1.5 h

6: 52 mg / aq. AcOH / Ambient temperature

With manganese(IV) oxide; potassium hydroxide; diisobutylaluminium hydride; acetic acid; toluene-4-sulfonic acid; In methanol; diethyl ether; hexane; dichloromethane; ethyl acetate;

DOI:10.1002/hlca.19900730426

Reference yield:

(+/-)-3,4-Dihydroxy-β-ionone (126585-77-1,130856-67-6,130856-73-4) → (2E,4E)-5-((3S,4R)-3,4-Dihydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal (130815-76-8,130856-71-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 3.16 g / TsOH / CH₂Cl₂ / 4 h

2: 1.2 g

3: 0.80 g / DIBAH / hexane; diethyl ether / 0 °C

4: 295 g / MnO₂ / ethyl acetate / 1.5 h

5: 52 mg / aq. AcOH / Ambient temperature

With manganese(IV) oxide; diisobutylaluminium hydride; acetic acid; toluene-4-sulfonic acid; In diethyl ether; hexane; dichloromethane; ethyl acetate;

DOI:10.1002/hlca.19900730426

upstream raw materials:

(+/-)-5-<3',4'-(Benzylidendioxy)-3',4'-dihydroxy-2',6',6'-trimethylcyclohex-1'-enyl>-3-methylpenta-2,4-dienal

(E)-4-(1',6'-Epoxy-2',2',6'-trimethyl-4'-cyclohexen-1'-yl)-3-buten-2-on

Acetic acid 6-acetoxy-2,4,4-trimethyl-3-((E)-3-oxo-but-1-enyl)-cyclohex-2-enyl ester

(+/-)-4-<3',4'-(Benzylidendioxy)-3',4'-dihydroxy-2',6',6'-trimethylcyclohex-1'-enyl>but-3-en-2-on

Downstream raw materials:

(+/-)-β,β-Carotin-cis,cis-3,4,3',4'-tetrol

(+/-)-Essigsaeure-<6-acetoxy-3-(3'-methyl-5'-oxopenta-1',3'-dienyl)-2,4,4-trimethylcyclohex-2-enyl>ester