Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester
• CAS No.: 136804-25-6
• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.387
• Mol file: 136804-25-6.mol

Synonyms:Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester

Chemical Property of Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester

There total 6 articles about Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl 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:

hex-2-en-5-yn-1-ol (214470-39-0) → Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester (136804-25-6)

Guidance literature:

Multi-step reaction with 6 steps

1: HN3)2>2, CuI / Pd(Ph₃)2Cl₂ / 20 °C

2: SOBr₂, propylen oxide / CH₂Cl₂ / 0 °C

3: 1) KOH / 1) H₂O, 2) MeOH, 20 deg C

4: Zn, Cu(OAc)2*H₂O, AgNO₃ / methanol; H₂O / 48 h / 20 °C

5: NEt₃, DMAP / CH₂Cl₂

6: ethanol / 60 h / Heating

With dmap; potassium hydroxide; copper(l) iodide; dibromo sulfoxide; copper diacetate; silver nitrate; triethylamine; diisopropylamine; methyloxirane; zinc; bis-triphenylphosphine-palladium(II) chloride; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jo00022a009

Reference yield:

Benzoic acid 5-[((2E,5Z)-octa-2,5,7-trienyl)oxy]-4-oxo-4H-pyran-2-ylmethyl ester (136804-29-0) → Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester (136804-25-6)

Guidance literature:

In ethanol; for 60h; Heating;

DOI:10.1021/jo00022a009

Reference yield:

(E)-8-Bromo-octa-1,6-dien-3-yne (136804-21-2) → Benzoic acid 5-hydroxy-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester (136804-25-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) KOH / 1) H₂O, 2) MeOH, 20 deg C

2: Zn, Cu(OAc)2*H₂O, AgNO₃ / methanol; H₂O / 48 h / 20 °C

3: NEt₃, DMAP / CH₂Cl₂

4: ethanol / 60 h / Heating

With dmap; potassium hydroxide; copper diacetate; silver nitrate; triethylamine; zinc; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jo00022a009

upstream raw materials:

Benzoic acid 5-[((2E,5Z)-octa-2,5,7-trienyl)oxy]-4-oxo-4H-pyran-2-ylmethyl ester

hex-2-en-5-yn-1-ol

(E)-8-Bromo-octa-1,6-dien-3-yne

2-Hydroxymethyl-5-[((2E,5Z)-octa-2,5,7-trienyl)oxy]-pyran-4-one

Downstream raw materials:

Benzoic acid (1S,6R,8R)-10-methoxy-11-oxo-2-vinyl-12-oxa-tricyclo[6.3.1.0^1,6]dodeca-4,9-dien-8-ylmethyl ester

Trifluoro-methanesulfonate6-benzoyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-((Z)-1-vinyl-hexa-3,5-dienyl)-pyranylium;

Trifluoro-methanesulfonate6-benzoyloxymethyl-3-hydroxy-4-methoxy-2-((Z)-1-vinyl-hexa-3,5-dienyl)-pyranylium;

Benzoic acid 5-(tert-butyl-dimethyl-silanyloxy)-4-oxo-6-((Z)-1-vinyl-hexa-3,5-dienyl)-4H-pyran-2-ylmethyl ester