1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8,9,10-tetrahydrobenzopyrene

Base Information

• Chemical Name: 1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8,9,10-tetrahydrobenzo
• Molecular Formula: C₃₆H₂₆O₆
• Molecular Weight: 554.599

Synonyms:

Chemical Property of 1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8,9,10-tetrahydrobenzo

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

There total 17 articles about 1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8,9,10-tetrahydrobenzopyrene 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:

1-methoxypyrene-8-carboxaldehyde (93656-82-7) → 1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8,9,10-tetrahydrobenzopyrene (119784-53-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / pyridine, piperidine / 1.) from 80 deg C to 85 deg C, 30 min, 2.) reflux, 4 h

2: H₂ / 10percent Pd/C / tetrahydrofuran / 5 h / 1810.02 Torr

3: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

4: Et₃N / CH₂Cl₂ / 0.25 h / 0 - 5 °C

5: aq. tricaprylylmethylammonium chloride / benzene / 15 h / Heating

6: aq. KOH / ethane-1,2-diol / 8 h / Heating

7: polyphosphoric acid / 1 h / 100 - 105 °C

8: 48percent aq. HBr, CH₃CO₂H / 2 h / Heating

9: NaBH₄ / ethanol / 0.5 h

10: p-toluenesulfonic acid / benzene / 1 h / Heating

11: pyridine / 3 h

12: 1.) I₂ / 1.) benzene, 2.) benzene, from RT to reflux, 80 min

With piperidine; pyridine; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; PPA; hydrogen bromide; hydrogen; iodine; Aliquat 336; toluene-4-sulfonic acid; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethylene glycol; benzene;

DOI:10.1021/jo00283a020

Reference yield:

3-(1-methoxypropen-8-yl)-2-propenoic acid → 1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8,9,10-tetrahydrobenzopyrene (119784-53-1)

Guidance literature:

Multi-step reaction with 11 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran / 5 h / 1810.02 Torr

2: LiAlH₄ / tetrahydrofuran / 0.5 h / Heating

3: Et₃N / CH₂Cl₂ / 0.25 h / 0 - 5 °C

4: aq. tricaprylylmethylammonium chloride / benzene / 15 h / Heating

5: aq. KOH / ethane-1,2-diol / 8 h / Heating

6: polyphosphoric acid / 1 h / 100 - 105 °C

7: 48percent aq. HBr, CH₃CO₂H / 2 h / Heating

8: NaBH₄ / ethanol / 0.5 h

9: p-toluenesulfonic acid / benzene / 1 h / Heating

10: pyridine / 3 h

11: 1.) I₂ / 1.) benzene, 2.) benzene, from RT to reflux, 80 min

With pyridine; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; PPA; hydrogen bromide; hydrogen; iodine; Aliquat 336; toluene-4-sulfonic acid; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethylene glycol; benzene;

DOI:10.1021/jo00283a020

Reference yield:

1-bromo-7,8,9,10-tetrahydrobenzopyrene-7-one ethylene ketal (119784-47-3) → 1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8,9,10-tetrahydrobenzopyrene (119784-53-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Mg, ethylene dibromide, 2.) B₂H₆, 3.) aq. NaOH, H₂O₂

2: NaBH₄ / ethanol / 0.5 h

3: p-toluenesulfonic acid / benzene / 1 h / Heating

4: pyridine / 3 h

5: 1.) I₂ / 1.) benzene, 2.) benzene, from RT to reflux, 80 min

With pyridine; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; iodine; toluene-4-sulfonic acid; magnesium; ethylene dibromide; diborane; In ethanol; benzene;

DOI:10.1021/jo00283a020

upstream raw materials:

silver benzoate

1-acetoxy-9,10-dihydrobenzopyrene

1-methoxypyrene-8-carboxaldehyde

1-hydroxy-7,8,9,10-tetrahydro-benzo(a)pyrene-7-one

Downstream raw materials:

1-acetoxy-trans-7,8-bis(benzoyloxy)-7,8-dihydrobenzopyrene

1-hydroxy-trans-7,8-dihydroxy-7,8-dihydrobenzopyrene

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