2-Pentenoic acid, 5-(acetyloxy)-4-(2-methoxy-4-methylphenyl)-, methyl ester, (E)-

Base Information

• Chemical Name: 2-Pentenoic acid, 5-(acetyloxy)-4-(2-methoxy-4-methylphenyl)-, methyl ester, (E)-
• CAS No.: 164921-78-2
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 164921-78-2.mol

Synonyms:

Chemical Property of 2-Pentenoic acid, 5-(acetyloxy)-4-(2-methoxy-4-methylphenyl)-, methyl ester, (E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Pentenoic acid, 5-(acetyloxy)-4-(2-methoxy-4-methylphenyl)-, methyl ester, (E)-

There total 1 articles about 2-Pentenoic acid, 5-(acetyloxy)-4-(2-methoxy-4-methylphenyl)-, methyl 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:

acetic anhydride (108-24-7) + methyl 4-(2'-methoxy-4'-methylphenyl)-5-hydroxy-(2E)-pentanoate (164921-74-8) → (E)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester (164921-78-2)

Guidance literature:

With pyridine;

DOI:10.1248/cpb.42.1590 DOI:10.1016/0957-4166(95)00229-I

Reference yield:

(E)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester (164921-78-2) → 2-[(1R)-1,5-dimethylhex-4-enyl]-5-methylphenol (17194-58-0,69350-75-0,70878-71-6,69301-27-5)

Guidance literature:

Multi-step reaction with 12 steps

1: immobilized lipase OF-360 / H₂O; diisopropyl ether / 72 h / 33 °C

2: 99 percent / MeONa / methanol / 1 h / 0 °C

3: H₂ / 20 percent Pd(OH)2-C / ethyl acetate / 20 °C

4: pyridine / 12 h / 20 °C

5: 26 percent / NaBH₄ / dimethylsulfoxide / 2 h / 80 °C

6: 90 percent / pyridine / 24 h / 20 °C

7: AlCl₃; EtSH / 0.5 h / 0 °C

8: NaH; 18-crown-16 / acetonitrile / 1 h / 0 °C

9: 98 percent / 2 M aq. NaOH / methanol / 0.17 h / 50 °C

10: PCC; Celite 545 / CH₂Cl₂ / 1 h / 20 °C

11: n-BuLi / hexane; tetrahydrofuran / 48 h / 20 °C

12: 62 percent / 2 M aq. HCl / propan-2-ol / 0.5 h / 60 °C

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; aluminium trichloride; 18-crown-16; Celite; immobilized lipase OF-360; hydrogen; sodium methylate; sodium hydride; pyridinium chlorochromate; ethanethiol; palladium hydroxide - carbon; In tetrahydrofuran; methanol; hexane; dichloromethane; di-isopropyl ether; water; dimethyl sulfoxide; ethyl acetate; isopropyl alcohol; acetonitrile; 1: racemate resolution;

DOI:10.1248/cpb.49.1581

Reference yield:

(E)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester (164921-78-2) → (4R)-(2-methoxy-4-methylphenyl)pentanol (170423-80-0)

Guidance literature:

Multi-step reaction with 5 steps

1: immobilized lipase OF-360 / H₂O; diisopropyl ether / 72 h / 33 °C

2: 99 percent / MeONa / methanol / 1 h / 0 °C

3: H₂ / 20 percent Pd(OH)2-C / ethyl acetate / 20 °C

4: pyridine / 12 h / 20 °C

5: 26 percent / NaBH₄ / dimethylsulfoxide / 2 h / 80 °C

With pyridine; sodium tetrahydroborate; immobilized lipase OF-360; hydrogen; sodium methylate; palladium hydroxide - carbon; In methanol; di-isopropyl ether; water; dimethyl sulfoxide; ethyl acetate; 1: racemate resolution;

DOI:10.1248/cpb.49.1581

upstream raw materials:

acetic anhydride

methyl 4-(2'-methoxy-4'-methylphenyl)-5-hydroxy-(2E)-pentanoate

Downstream raw materials:

methyl (4R)-(2-methoxy-4-methylphenyl)-5-hydroxyphenoate

methyl (4S)-(2-methoxy-4-methylpenyl)-5-hydroxypentanoate

(E)-(R)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester

(E)-(S)-5-Acetoxy-4-(2-methoxy-4-methyl-phenyl)-pent-2-enoic acid methyl ester