trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene

Base Information

• Chemical Name: trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene
• CAS No.: 88746-68-3
• Molecular Formula: C₃₄H₂₂O₄
• Molecular Weight: 494.546

Synonyms:trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene

Chemical Property of trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene

Chemical Property:

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Technology Process of trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene

There total 12 articles about trans-11,12-bis(benzoyloxy)-11,12-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: 50.0%

9-bromo-11β,12α-bis(benzoyloxy)-9,10,11,12-tetrahydrobenzofluoranthene (88746-67-2) → trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene (88746-68-3)

Guidance literature:

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

DOI:10.1021/jo00180a026

Reference yield:

2-methylfluoranthene (33543-31-6) → trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene (88746-68-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

2: 1.85 g / diethyl ether / 8 h

3: 1.) diborane, sodium hydroxide, 2.) H₂O₂ / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h

4: 82 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h

5: 62 percent / AgNO₃, NaOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

6: 1.8 g / oxalyl chloride / CH₂Cl₂ / 3 h / Ambient temperature

7: AlCl₃ / CS₂ / 1.) 0 deg C , 1h, 2.) reflux , 30 min

8: 0.8 g / lithium aluminumhydride / tetrahydrofuran / 1 h / Ambient temperature

9: 72 percent / HCl / acetic acid / 1 h / 90 °C

10: 60 percent / I₂ / benzene / 3 h / Heating

11: 60 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

12: 50 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 3 h / 0 °C

With sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; Perbenzoic acid; oxalyl dichloride; DBN; dihydrogen peroxide; iodine; silver nitrate; pyridinium chlorochromate; diborane; hydrogenchloride; In tetrahydrofuran; carbon disulfide; tetrachloromethane; diethyl ether; dichloromethane; water; acetic acid; benzene;

DOI:10.1021/jo00180a026

Reference yield:

4-(2-fluoranthenyl)-1-butene (88746-59-2) → trans-11,12-bis(benzoyloxy)-11,12-dihydrobenzofluoranthene (88746-68-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) diborane, sodium hydroxide, 2.) H₂O₂ / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h

2: 82 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h

3: 62 percent / AgNO₃, NaOH / tetrahydrofuran; H₂O / 2 h / Ambient temperature

4: 1.8 g / oxalyl chloride / CH₂Cl₂ / 3 h / Ambient temperature

5: AlCl₃ / CS₂ / 1.) 0 deg C , 1h, 2.) reflux , 30 min

6: 0.8 g / lithium aluminumhydride / tetrahydrofuran / 1 h / Ambient temperature

7: 72 percent / HCl / acetic acid / 1 h / 90 °C

8: 60 percent / I₂ / benzene / 3 h / Heating

9: 60 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 1.5 h / Heating; Irradiation

10: 50 percent / 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 3 h / 0 °C

With sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; Perbenzoic acid; oxalyl dichloride; DBN; dihydrogen peroxide; iodine; silver nitrate; pyridinium chlorochromate; diborane; hydrogenchloride; In tetrahydrofuran; carbon disulfide; tetrachloromethane; dichloromethane; water; acetic acid; benzene;

DOI:10.1021/jo00180a026

upstream raw materials:

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

2-methylfluoranthene

4-(2-fluoranthenyl)-1-butene

9,10-dihydrobenzofluoranthene

Downstream raw materials:

cis-11,12-dihydro-11,12-dihydroxybenzofluoranthene

trans-11,12-dihydro-11,12-dihydroxybenzofluoranthene

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