15-hydroperoxyabietic acid

Base Information

• Chemical Name: 15-hydroperoxyabietic acid
• CAS No.: 113903-96-1
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Mol file: 113903-96-1.mol

Synonyms:1-Phenanthrenecarboxylicacid,1,2,3,4,4a,4b,5,6,10,10a-decahydro-7-(1-hydroperoxy-1-methylethyl)-1,4a-dimethyl-,[1R-(1a,4ab,4ba,10aa)]-; 15-Hydroperoxyabietic acid

Chemical Property of 15-hydroperoxyabietic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 461.3°Cat760mmHg
• Flash Point: 156.9°C
• PSA: 66.76000
• Density: 1.12g/cm³
• LogP: 4.81840

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 15-hydroperoxyabietic acid

There total 7 articles about 15-hydroperoxyabietic acid 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: 63.0%

15-hydroxyabietic acid (101821-23-2) → 7-(1-hydroperoxy-1-methyl-ethyl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid (113903-96-1)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; In dichloromethane; at 0 ℃; for 10h;

DOI:10.1055/s-2001-18089

Reference yield:

13-Oxopodocarp-8(14)-en-18-saeure-methylester (20085-81-8) → 7-(1-hydroperoxy-1-methyl-ethyl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid (113903-96-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / t-BuOK / dimethylsulfoxide / 0.75 h / 20 °C

2.1: 74 percent / (COBr)2; DMF / CH₂Cl₂ / 5.25 h / -78 - 20 °C

3.1: t-BuLi / diethyl ether; pentane / 1.5 h / -78 °C

3.2: 70 percent / diethyl ether; pentane / 2 h / 20 °C

4.1: 63 percent / aq. H₂O₂; H₂SO₄ / CH₂Cl₂ / 10 h / 0 °C

With Oxalyl bromide; sulfuric acid; potassium tert-butylate; dihydrogen peroxide; tert.-butyl lithium; N,N-dimethyl-formamide; In diethyl ether; dichloromethane; dimethyl sulfoxide; pentane;

DOI:10.1055/s-2001-18089

Reference yield:

methyl abieta-8,13(15)-dien-18-oate (19402-34-7) → 7-(1-hydroperoxy-1-methyl-ethyl)-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,10,10a-decahydro-phenanthrene-1-carboxylic acid (113903-96-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / MCPBA / CH₂Cl₂ / 2 h / 0 °C

2.1: 87 percent / H₅IO₆ / tetrahydrofuran / 1 h / -30 - -10 °C

3.1: 96 percent / HCl / methanol / 4 h / 0 °C

4.1: 80 percent / t-BuOK / dimethylsulfoxide / 0.75 h / 20 °C

5.1: 74 percent / (COBr)2; DMF / CH₂Cl₂ / 5.25 h / -78 - 20 °C

6.1: t-BuLi / diethyl ether; pentane / 1.5 h / -78 °C

6.2: 70 percent / diethyl ether; pentane / 2 h / 20 °C

7.1: 63 percent / aq. H₂O₂; H₂SO₄ / CH₂Cl₂ / 10 h / 0 °C

With hydrogenchloride; Oxalyl bromide; sulfuric acid; potassium tert-butylate; dihydrogen peroxide; tert.-butyl lithium; periodic acid; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane;

DOI:10.1055/s-2001-18089

upstream raw materials:

15-hydroxyabietic acid

13-Oxopodocarp-8⁽¹⁴⁾-en-18-saeure-methylester

methyl abieta-8,13⁽¹⁵⁾-dien-18-oate

13-oxo-13-deisopropyl-abiet-8⁽¹⁴⁾en-15-oic acid

Downstream raw materials:

13β,15-epoxy-14α-hydroxy-abiet-7-en-19-oic acid

13-oxo-13-deisopropyl-abiet-8⁽¹⁴⁾en-15-oic acid

15-hydroxyabietic acid

7α-(1',1',3',3'-tetramethyl-1',3'-dihydroisoindol-2'-yloxy)-13-oxo-13-deisopropyl-abiet-8(14)-en-15-oic acid

Refernces