3-(8,11,13-Pentadecatrienyl)pyrocatechol

Base Information

• Chemical Name: 3-(8,11,13-Pentadecatrienyl)pyrocatechol
• CAS No.: 21104-16-5
• Molecular Formula: C21H30O2
• Molecular Weight: 314.4617
• Nikkaji Number: J387.680B,J39.040B
• Mol file: 21104-16-5.mol

Synonyms:3-(8,11,13-Pentadecatrienyl)pyrocatechol;21104-16-5;Pyrocatechol, 3-(8,11,13-pentadecatrienyl)-;SCHEMBL14947767;3-[(8Z,11E,13E)-8,11,13-Pentadecatrienyl]catechol

Chemical Property of 3-(8,11,13-Pentadecatrienyl)pyrocatechol

Chemical Property:

• Vapor Pressure: 9.53E-10mmHg at 25°C
• Boiling Point: 477.6°C at 760 mmHg
• Flash Point: 212.2°C
• Density: 0.999g/cm³
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 357

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)O
• Isomeric SMILES: C/C=C/C=C/C/C=C/CCCCCCCC1=C(C(=CC=C1)O)O

Technology Process of 3-(8,11,13-Pentadecatrienyl)pyrocatechol

There total 8 articles about 3-(8,11,13-Pentadecatrienyl)pyrocatechol 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: 65.0%

3-<(8Z,11E,13E)-8,11,13-pentadecatrienyl>catechol diacetate (136788-24-4) → 3-<(8Z,11E,13E)-8,11,13-pentadecatrienyl>catechol (83532-39-2,21104-16-5)

Guidance literature:

With lithium aluminium tetrahydride; tert-butyl alcohol; In tetrahydrofuran; at -50 ℃;

DOI:10.1246/bcsj.64.2560

Reference yield:

1,2-dimethoxybenzene (91-16-7) → 3-<(8Z,11E,13E)-8,11,13-pentadecatrienyl>catechol (83532-39-2,21104-16-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) BuLi / 1) THF, hexane, 2h, RT, 2) THF, 5h, reflux

2: 92 percent / BBr₃ / CH₂Cl₂ / 12 h / 0 deg C to RT

3: 76 percent / pyridine / 4 h / 100 °C

4: 88 percent / NaI / acetone / 3 h / 60 °C

5: 71 percent / NaHCO₃, DMSO / benzene / 4 h / 90 °C

6: 1) BuLi / 1) hexane, benzene, 20 deg C, 2) benzene, 25 deg C

7: 65 percent / LiAlH₄, t-BuOH / tetrahydrofuran / -50 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; boron tribromide; sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; acetone; benzene;

DOI:10.1246/bcsj.64.2560

Reference yield:

1,8-dibromooctane (4549-32-0) → 3-<(8Z,11E,13E)-8,11,13-pentadecatrienyl>catechol (83532-39-2,21104-16-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) BuLi / 1) THF, hexane, 2h, RT, 2) THF, 5h, reflux

2: 92 percent / BBr₃ / CH₂Cl₂ / 12 h / 0 deg C to RT

3: 76 percent / pyridine / 4 h / 100 °C

4: 88 percent / NaI / acetone / 3 h / 60 °C

5: 71 percent / NaHCO₃, DMSO / benzene / 4 h / 90 °C

6: 1) BuLi / 1) hexane, benzene, 20 deg C, 2) benzene, 25 deg C

7: 65 percent / LiAlH₄, t-BuOH / tetrahydrofuran / -50 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; boron tribromide; sodium hydrogencarbonate; dimethyl sulfoxide; sodium iodide; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; acetone; benzene;

DOI:10.1246/bcsj.64.2560

upstream raw materials:

3-<(8Z,11E,13E)-8,11,13-pentadecatrienyl>catechol diacetate

1,2-dimethoxybenzene

1,8-dibromooctane

3-(8-oxooctyl)catechol diacetate

Downstream raw materials:

3-(Pentadeca-8',11',13'-trienyl)-veratrol

Refernces