2,5-Cyclohexadiene-1,4-dione, 2,3-dimethyl-5-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22, 26,30,34-hexatriacontanonaenyl)-

Base Information

• Chemical Name: 2,5-Cyclohexadiene-1,4-dione, 2,3-dimethyl-5-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22, 26,30,34-hexatriacontanonaenyl)-
• CAS No.: 66408-53-5
• Molecular Formula: C₅₃H₈₀O₂
• Molecular Weight: 749.217
• Mol file: 66408-53-5.mol

Synonyms:

Chemical Property of 2,5-Cyclohexadiene-1,4-dione, 2,3-dimethyl-5-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22, 26,30,34-hexatriacontanonaenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-Cyclohexadiene-1,4-dione, 2,3-dimethyl-5-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22, 26,30,34-hexatriacontanonaenyl)-

There total 12 articles about 2,5-Cyclohexadiene-1,4-dione, 2,3-dimethyl-5-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22, 26,30,34-hexatriacontanonaenyl)- 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:

2-methoxycarbonyl-3-methyl-6,N-bis(trisopropylsilyl)aniline (476170-47-5) → plastoquinone-9 (24584-03-0,66408-53-5,4299-57-4,1184-38-9,26013-03-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 91 percent / KF; HCl; water / methanol / 2 h / Heating

2.1: 75 percent / Red-Al / toluene / 3 h / Heating

3.1: H₂SO₄; NaNO₂ / H₂O / 0.08 h

3.2: 77 percent / CuSO₄*5H₂O; Cu₂O / H₂O / 0.75 h

4.1: 84 percent / iron; bromine / CH₂Cl₂ / 20 °C

5.1: 51 percent / 2,6-pyridinedicarboxylic acid; ammonium cerium(VI) nitrate / acetonitrile; H₂O

6.1: 59 percent / BF₃*OEt₂; silver oxide / CH₂Cl₂ / 2 h / -80 - -20 °C

7.1: 0.26 g / Na₂S₂O₄; NaOH; water / diethyl ether

8.1: 0.30 g / NaH / tetrahydrofuran / 3.5 h

9.1: butyllithium / diethyl ether; hexane / 0.17 h / -70 °C

9.2: 0.29 g / H₂O

10.1: 0.15 g / 2,6-pyridinedicarboxylic acid; ammonium cerium(VI) nitrate / H₂O; acetonitrile

With hydrogenchloride; potassium fluoride; sodium hydroxide; n-butyllithium; sodium dithionite; Pyridine-2,6-dicarboxylic acid; ammonium cerium(VI) nitrate; sulfuric acid; boron trifluoride diethyl etherate; water; bromine; iron; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; silver(l) oxide; sodium nitrite; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/1099-0690(200207)2002:13<2094::AID-EJOC2094>3.0.CO;2-E

Reference yield:

1,4-di-O-bis(methoxymethyl)-1,4-dihydroxy-2,3-dimethyl-5-[(all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl]benzene (476170-44-2) → plastoquinone-9 (24584-03-0,66408-53-5,4299-57-4,1184-38-9,26013-03-6)

Guidance literature:

With Pyridine-2,6-dicarboxylic acid; ammonium cerium(VI) nitrate; In water; acetonitrile;

DOI:10.1002/1099-0690(200207)2002:13<2094::AID-EJOC2094>3.0.CO;2-E

Reference yield:

2,3-Dimethylphenol (526-75-0) → plastoquinone-9 (24584-03-0,66408-53-5,4299-57-4,1184-38-9,26013-03-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 84 percent / iron; bromine / CH₂Cl₂ / 20 °C

2.1: 51 percent / 2,6-pyridinedicarboxylic acid; ammonium cerium(VI) nitrate / acetonitrile; H₂O

3.1: 59 percent / BF₃*OEt₂; silver oxide / CH₂Cl₂ / 2 h / -80 - -20 °C

4.1: 0.26 g / Na₂S₂O₄; NaOH; water / diethyl ether

5.1: 0.30 g / NaH / tetrahydrofuran / 3.5 h

6.1: butyllithium / diethyl ether; hexane / 0.17 h / -70 °C

6.2: 0.29 g / H₂O

7.1: 0.15 g / 2,6-pyridinedicarboxylic acid; ammonium cerium(VI) nitrate / H₂O; acetonitrile

With sodium hydroxide; n-butyllithium; sodium dithionite; Pyridine-2,6-dicarboxylic acid; ammonium cerium(VI) nitrate; boron trifluoride diethyl etherate; water; bromine; iron; sodium hydride; silver(l) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile;

DOI:10.1002/1099-0690(200207)2002:13<2094::AID-EJOC2094>3.0.CO;2-E

upstream raw materials:

1,4-di-O-bis(methoxymethyl)-1,4-dihydroxy-2,3-dimethyl-5-[(all-E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl]benzene

2,3-Dimethylphenol

5-bromo-2,3-dimethylcyclohexa-2,5-diene-1,4-dione

2,4-dibromo-5,6-dimethylphenol

Refernces