trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene

Base Information

• Chemical Name: trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene
• CAS No.: 77061-17-7
• Molecular Formula: C₃₄H₂₂O₄
• Molecular Weight: 494.546
• Mol file: 77061-17-7.mol

Synonyms:trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene

Chemical Property of trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene

There total 13 articles about trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene 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: 60.0%

12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene (77061-16-6) → trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene (77061-17-7)

Guidance literature:

With DBN; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/jo00325a028

Reference yield:

7-methyl-6b,7,10,10a-tetrahydrofluoranthene (77096-72-1) → trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene (77061-17-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 80 percent / DDQ / xylene / 5 h / Heating

2: 80 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 3 h / Heating

3: 78 percent / diethyl ether / 30 h / Heating

4: 1.) diborane, 2.) 30percent H₂O₂ / 1.) THF, from 0 deg C to room temp., 8 h, 2.) reflux, 1 h

5: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

6: 85 percent / AgNO₃, 1.5 KOH / ethanol; H₂O / 2 h

7: SOCl₂ / benzene / 3 h / Heating

8: 1.) AlCl₃ / CS₂ / 1.) 0 deg C, 2.) reflux, 10 min

9: LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

10: 60 percent / conc. H₂SO₄ / acetic acid / 3 h / 60 °C

11: 62 percent / 1.) I₂ / benzene / 1.) reflux, 2.) reflux, 2.5 h

12: 30 percent / N-bromsuccinimide, α,α'-azobis(isobutyronitrile) / CCl4 / 2 h / Heating

13: 60 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 3 h / 0 °C

With potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; thionyl chloride; Perbenzoic acid; sulfuric acid; azobisisobutyronitrile; DBN; dihydrogen peroxide; iodine; silver nitrate; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diborane; In tetrahydrofuran; carbon disulfide; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; xylene; benzene;

DOI:10.1021/jo00325a028

Reference yield:

7-methylfluoranthene (23339-05-1) → trans-9,10-bis(benzoyloxy)-9,10-dihydrobenzofluoranthene (77061-17-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 80 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 3 h / Heating

2: 78 percent / diethyl ether / 30 h / Heating

3: 1.) diborane, 2.) 30percent H₂O₂ / 1.) THF, from 0 deg C to room temp., 8 h, 2.) reflux, 1 h

4: pyridinium chlorochromate / CH₂Cl₂ / 1 h / 20 °C

5: 85 percent / AgNO₃, 1.5 KOH / ethanol; H₂O / 2 h

6: SOCl₂ / benzene / 3 h / Heating

7: 1.) AlCl₃ / CS₂ / 1.) 0 deg C, 2.) reflux, 10 min

8: LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

9: 60 percent / conc. H₂SO₄ / acetic acid / 3 h / 60 °C

10: 62 percent / 1.) I₂ / benzene / 1.) reflux, 2.) reflux, 2.5 h

11: 30 percent / N-bromsuccinimide, α,α'-azobis(isobutyronitrile) / CCl4 / 2 h / Heating

12: 60 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 3 h / 0 °C

With potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; thionyl chloride; Perbenzoic acid; sulfuric acid; azobisisobutyronitrile; DBN; dihydrogen peroxide; iodine; silver nitrate; pyridinium chlorochromate; diborane; In tetrahydrofuran; carbon disulfide; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; benzene;

DOI:10.1021/jo00325a028

upstream raw materials:

12-bromo-9α,10β-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene

7-methyl-6b,7,10,10a-tetrahydrofluoranthene

7-methylfluoranthene

4-(7-fluoranthenyl)-1-butene

Downstream raw materials:

trans-9,10-dihydro-9,10-dihydroxybenzofluoranthene

Refernces