(E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester

Base Information

• Chemical Name: (E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester
• CAS No.: 137349-54-3
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333

Synonyms:(E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester

Chemical Property of (E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester

There total 3 articles about (E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid 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: 67.0%

(E)-5-((1S,6R)-1-Hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynoic acid methyl ester (130583-85-6,137432-92-9,137432-94-1,143062-36-6,143062-37-7,145774-46-5,145774-55-6) → (E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester (137349-54-3)

Guidance literature:

With potassium hydrogensulfate; acetic anhydride; In acetic acid; at 70 ℃; for 1.75h;

DOI:10.1016/0031-9422(91)83174-J

Reference yield:

2-trans-5-(1'-hydroxy-2',2',6'-trimethyl-4'-oxocyclohexyl)-3-methylpent-2-en-4-yn-1-ol (49846-56-2,70954-44-8,95343-49-0,95343-61-6,130694-57-4,130694-71-2,130694-74-5,137432-91-8,137432-93-0) → (E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester (137349-54-3)

Guidance literature:

Multi-step reaction with 3 steps

1: MnO₂ / acetone / 1 h / Ambient temperature

2: MnO₂, NaCN, HOAc / 2 h

3: 67 percent / Ac₂O, KHSO₄ / acetic acid / 1.75 h / 70 °C

With manganese(IV) oxide; potassium hydrogensulfate; sodium cyanide; acetic anhydride; acetic acid; In acetic acid; acetone;

DOI:10.1016/0031-9422(91)83174-J

Reference yield:

(E)-5-((1S,6R)-1-Hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynal (130583-81-2,145774-47-6,145774-56-7) → (E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-1-enyl)-pent-2-en-4-ynoic acid methyl ester (137349-54-3)

Guidance literature:

Multi-step reaction with 2 steps

1: MnO₂, NaCN, HOAc / 2 h

2: 67 percent / Ac₂O, KHSO₄ / acetic acid / 1.75 h / 70 °C

With manganese(IV) oxide; potassium hydrogensulfate; sodium cyanide; acetic anhydride; acetic acid; In acetic acid;

DOI:10.1016/0031-9422(91)83174-J

upstream raw materials:

(E)-5-((1S,6R)-1-Hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynoic acid methyl ester

2-trans-5-(1'-hydroxy-2',2',6'-trimethyl-4'-oxocyclohexyl)-3-methylpent-2-en-4-yn-1-ol

(E)-5-((1S,6R)-1-Hydroxy-2,2,6-trimethyl-4-oxo-cyclohexyl)-3-methyl-pent-2-en-4-ynal

Downstream raw materials:

(E)-3-Methyl-5-(2,6,6-trimethyl-4-oxo-cyclohex-2-enylidene)-penta-2,4-dienoic acid methyl ester

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