2-Butenoic acid, 3-methyl-, 2-methyl-2-butenyl ester, (E)-

Base Information

• Chemical Name: 2-Butenoic acid, 3-methyl-, 2-methyl-2-butenyl ester, (E)-
• CAS No.: 90358-43-3
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.236
• Mol file: 90358-43-3.mol

Synonyms:

Chemical Property of 2-Butenoic acid, 3-methyl-, 2-methyl-2-butenyl ester, (E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Butenoic acid, 3-methyl-, 2-methyl-2-butenyl ester, (E)-

There total 1 articles about 2-Butenoic acid, 3-methyl-, 2-methyl-2-butenyl ester, (E)- 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: 90.0%

(E)-2-methyl-2-buten-1-ol (497-02-9) + 3-Methylbutenoic acid (541-47-9) → (2'E)-2'-methylbut-2-enyl 3-methylbut-2-enoate (90358-43-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/(sici)1099-0690(199911)1999:11<2781::aid-ejoc2781>3.0.co;2-c

Reference yield:

(2'E)-2'-methylbut-2-enyl 3-methylbut-2-enoate (90358-43-3) → (4S,5S)-2-((6S,7S)-3,5,5,6,7,8,8-Heptamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-1,3-dimethyl-4,5-diphenyl-imidazolidine

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / lithium cyclohexylisopropylamide; chlorotrimethylsilane / tetrahydrofuran

2: 67 percent / AlCl₃ / 1 h / 15 - 25 °C

3: 91 percent / LiAlH₄ / diethyl ether / 2.17 h / Heating

4: 90 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 2 h / 20 °C

5: 93 percent / KO(t-Bu) / 2-methyl-propan-2-ol / 24 h / 20 °C

6: 90 percent / LiAlH₄ / diethyl ether / 2 h / -40 °C

7: 5 percent / N,N-dimethylpyridine-4-amine / pyridine / 1 h / 0 - 20 °C

8: 84 percent / KOH / ethanol; H₂O / 15 h / 80 °C

9: 2.53 g / pyridine / 24 h / 5 - 20 °C

10: 65 percent / LiBHEt₃ / tetrahydrofuran / 4 h / 0 - 20 °C

11: 78 percent / Ce(NH₄)2(NO₃)6 / methanol / 55 °C

12: 4 Angstroem molecular sieves / diethyl ether / 20 °C

With dmap; potassium hydroxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; aluminium trichloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; Celite; potassium tert-butylate; lithium triethylborohydride; lithium cyclohexylisopropylamide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1002/1522-2675(200202)85:2<533::AID-HLCA533>3.0.CO;2-5

Reference yield:

(2'E)-2'-methylbut-2-enyl 3-methylbut-2-enoate (90358-43-3) → Toluene-4-sulfonic acid (2R,3R)-1,1,3,4,4,6,7-heptamethyl-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / lithium cyclohexylisopropylamide; chlorotrimethylsilane / tetrahydrofuran

2: 67 percent / AlCl₃ / 1 h / 15 - 25 °C

3: 91 percent / LiAlH₄ / diethyl ether / 2.17 h / Heating

4: 90 percent / pyridinium chlorochromate; celite / CH₂Cl₂ / 2 h / 20 °C

5: 93 percent / KO(t-Bu) / 2-methyl-propan-2-ol / 24 h / 20 °C

6: 90 percent / LiAlH₄ / diethyl ether / 2 h / -40 °C

7: 5 percent / N,N-dimethylpyridine-4-amine / pyridine / 1 h / 0 - 20 °C

8: pyridine / 24 h / 5 - 20 °C

With dmap; lithium aluminium tetrahydride; chloro-trimethyl-silane; aluminium trichloride; Celite; potassium tert-butylate; lithium cyclohexylisopropylamide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1002/1522-2675(200202)85:2<533::AID-HLCA533>3.0.CO;2-5

upstream raw materials:

(E)-2-methyl-2-buten-1-ol

3-Methylbutenoic acid

Downstream raw materials:

rel-(6R,7S)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethylnaphthalene-2-carbaldehyde

(+)-(6R,7R)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethylnaphthalene-2-carbaldehyde

(-)-(6S,7S)-5,6,7,8-tetrahydro-3,5,5,6,7,8,8-heptamethylnaphthalene-2-carbaldehyde

Refernces