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

Base Information

• Chemical Name: 1-hydroxy-trans-7,8-dihydroxy-7,8-dihydrobenzo
• Molecular Formula: C₂₀H₁₄O₃
• Molecular Weight: 302.329

Synonyms:

Chemical Property of 1-hydroxy-trans-7,8-dihydroxy-7,8-dihydrobenzo

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

There total 19 articles about 1-hydroxy-trans-7,8-dihydroxy-7,8-dihydrobenzopyrene 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-hydroxy-trans-7,8-dihydroxy-7,8-dihydrobenzopyrene (119784-57-5)

Guidance literature:

Multi-step reaction with 14 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

13: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 4 h / Heating

14: NaOH / methanol; tetrahydrofuran / 1 h / Ambient temperature

With piperidine; pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; PPA; hydrogen bromide; hydrogen; iodine; Aliquat 336; toluene-4-sulfonic acid; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethylene glycol; benzene;

DOI:10.1021/jo00283a020

Reference yield:

3-(1-methoxypropen-8-yl)-2-propenoic acid → 1-hydroxy-trans-7,8-dihydroxy-7,8-dihydrobenzopyrene (119784-57-5)

Guidance literature:

Multi-step reaction with 13 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

12: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 4 h / Heating

13: NaOH / methanol; tetrahydrofuran / 1 h / Ambient temperature

With pyridine; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; PPA; hydrogen bromide; hydrogen; iodine; Aliquat 336; toluene-4-sulfonic acid; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethylene glycol; benzene;

DOI:10.1021/jo00283a020

Reference yield:

1-hydroxy-7,8,9,10-tetrahydro-benzo(a)pyrene-7-one (119784-49-5) → 1-hydroxy-trans-7,8-dihydroxy-7,8-dihydrobenzopyrene (119784-57-5)

Guidance literature:

Multi-step reaction with 6 steps

1: NaBH₄ / ethanol / 0.5 h

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

3: pyridine / 3 h

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

5: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 4 h / Heating

6: NaOH / methanol; tetrahydrofuran / 1 h / Ambient temperature

With pyridine; sodium hydroxide; sodium tetrahydroborate; iodine; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; benzene;

DOI:10.1021/jo00283a020

upstream raw materials:

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

1-methoxypyrene-8-carboxaldehyde

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

1-acetoxy-9,10-dihydrobenzopyrene

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