12,14-DICHLORODEHYDROABIETIC ACID

Base Information

• Chemical Name: 12,14-DICHLORODEHYDROABIETIC ACID
• CAS No.: 65281-77-8
• Molecular Formula: C₂₀H₂₆Cl₂O₂
• Molecular Weight: 369.331
• Mol file: 65281-77-8.mol

Synonyms:1-Phenanthrenecarboxylic acid,6,8-dichloro-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-,(1R,4aS,10aR);12,14-DICHLORODEHYDROABIETIC ACID;

Chemical Property of 12,14-DICHLORODEHYDROABIETIC ACID

Chemical Property:

• Vapor Pressure: 1.27E-09mmHg at 25°C
• Melting Point: 222 - 237°C
• Boiling Point: 469.6°Cat760mmHg
• Flash Point: 237.8°C
• PSA: 37.30000
• Density: 1.2g/cm³
• LogP: 6.21170
• Storage Temp.: 4°C, Inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

95% ^*data from raw suppliers

12,14-Dichlorodehydroabieticacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 12,14-Dichlorodehydroabietic acid is a GABAA receptor inhibitor found in resin acids. It has been used as a flocculation agent of in analytical pre-concentration steps. It is also a known chloro-organic pollutant found in paper mills wastewater.

Technology Process of 12,14-DICHLORODEHYDROABIETIC ACID

There total 1 articles about 12,14-DICHLORODEHYDROABIETIC 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: 39.0%

dehydroabietic acid (1740-19-8) → 12,14-Dichlorodehydroabietic acid (65281-77-8)

Guidance literature:

With tetrachloromethane; iron(III) chloride; silica gel; chlorine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;

DOI:10.1016/j.bmcl.2008.10.078

Reference yield:

12,14-Dichlorodehydroabietic acid (65281-77-8) → 12,14-dichloro-13-isopropyl-8,11a-dimethyl-6-oxo-5-(5-phenylpent-4-ynyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[b,d]azepine-8-carboxylic acid methyl ester (915151-14-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / methanol; toluene; diethyl ether / 0.58 h / 20 °C

2: 82 percent / CrO₃; Ac₂O; acetic acid / 9 h / 50 °C

3: 207 mg / pyridine; NH₂OH*HCl / ethanol / 3.5 h / 100 °C

4: 99 percent / pyridine / 17 h / 20 °C

5: 81 percent / trifluoroacetic acid / 1 h / 20 °C

6: 74 percent / NaH / dimethylformamide / 17 h / 20 °C

7: 37 mg / CuI; triethylamine / Pd(PPh₃)2Cl₂ / 14 h / 20 °C

With pyridine; chromium(VI) oxide; copper(l) iodide; hydroxylamine hydrochloride; acetic anhydride; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; In methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene; 5: Beckmann rearrangement / 7: Sonogashira coupling;

DOI:10.1016/j.bmc.2006.07.042

Reference yield:

12,14-Dichlorodehydroabietic acid (65281-77-8) → 12,14-dichloro-13-isopropyl-8,11a-dimethyl-6-oxo-5-(5-phenylpent-4-ynyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[b,d]azepine-8-carboxylic acid

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / methanol; toluene; diethyl ether / 0.58 h / 20 °C

2: 82 percent / CrO₃; Ac₂O; acetic acid / 9 h / 50 °C

3: 207 mg / pyridine; NH₂OH*HCl / ethanol / 3.5 h / 100 °C

4: 99 percent / pyridine / 17 h / 20 °C

5: 81 percent / trifluoroacetic acid / 1 h / 20 °C

6: 74 percent / NaH / dimethylformamide / 17 h / 20 °C

7: 37 mg / CuI; triethylamine / Pd(PPh₃)2Cl₂ / 14 h / 20 °C

8: 87 percent / KOH; 18-crown ether-6 / methanol / 15 h / 80 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; copper(l) iodide; 18-crown-6 ether; hydroxylamine hydrochloride; acetic anhydride; sodium hydride; acetic acid; triethylamine; trifluoroacetic acid; bis-triphenylphosphine-palladium(II) chloride; In methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene; 5: Beckmann rearrangement / 7: Sonogashira coupling;

DOI:10.1016/j.bmc.2006.07.042

upstream raw materials:

dehydroabietic acid

Downstream raw materials:

12,14-dichloro-13-isopropyl-7-tosyloxyiminepodocarpe-8,11,13-triene-15-carboxylic acid methyl ester

12,14-dichloro-13-isopropyl-8,11a-dimethyl-6-oxo-5-(5-phenylpent-4-ynyl)-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[b,d]azepine-8-carboxylic acid methyl ester

12,14-dichloro-13-isopropyl-8,11a-dimethyl-6-oxo-5-[5-(3-iodophenyl)pent-4-ynyl]-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[b,d]azepine-8-carboxylic acid methyl ester

12,14-dichloro-13-isopropyl-8,11a-dimethyl-6-oxo-5-[5-(4-iodophenyl)pent-4-ynyl]-6,7,7a,8,9,10,11,11a-octahydro-5H-dibenzo[b,d]azepine-8-carboxylic acid methyl ester