(1aα,2β,7bα)-1,1-Dichloro-2-(benzoyloxy)-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalene

Base Information

• Chemical Name: (1aα,2β,7bα)-1,1-Dichloro-2-(benzoyloxy)-1a,2,3,7b-tetrahydro-1H-cyclopropa
• Molecular Formula: C₁₈H₁₄Cl₂O₂
• Molecular Weight: 333.214

Synonyms:

Chemical Property of (1aα,2β,7bα)-1,1-Dichloro-2-(benzoyloxy)-1a,2,3,7b-tetrahydro-1H-cyclopropa

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

There total 6 articles about (1aα,2β,7bα)-1,1-Dichloro-2-(benzoyloxy)-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalene 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:

1,4-dihydronaphthalene (612-17-9) → (1aα,2β,7bα)-1,1-Dichloro-2-(benzoyloxy)-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalene (132316-83-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / N-bromosuccinimide, H₂O / dimethylsulfoxide / 0.75 h / 5 °C

2: 90 percent / pyridine / 24 h / 0 °C

3: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / tetrahydrofuran / 16 h / Ambient temperature

4: benzyltriethyl ammonium chloride (TEBAC), 50percent aq. NaOH / 40 h / Ambient temperature

5: NaOH / methanol / 3 h / Ambient temperature

6: pyridine / methanol

With pyridine; sodium hydroxide; N-Bromosuccinimide; DBN; N-benzyl-N,N,N-triethylammonium chloride; water; In tetrahydrofuran; pyridine; methanol; dimethyl sulfoxide;

DOI:10.1021/jo00006a015

Reference yield:

(2α,3β)-2-Hydroxy-3-bromo-1,2,3,4-tetrahydronaphthalene (101751-92-2,103038-41-1) → (1aα,2β,7bα)-1,1-Dichloro-2-(benzoyloxy)-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalene (132316-83-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine / 24 h / 0 °C

2: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / tetrahydrofuran / 16 h / Ambient temperature

3: benzyltriethyl ammonium chloride (TEBAC), 50percent aq. NaOH / 40 h / Ambient temperature

4: NaOH / methanol / 3 h / Ambient temperature

5: pyridine / methanol

With pyridine; sodium hydroxide; DBN; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/jo00006a015

Reference yield:

(2α,3β)-2-Acetoxy-3-bromo-1,2,3,4-tetrahydronaphthalene (132316-79-1) → (1aα,2β,7bα)-1,1-Dichloro-2-(benzoyloxy)-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalene (132316-83-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / tetrahydrofuran / 16 h / Ambient temperature

2: benzyltriethyl ammonium chloride (TEBAC), 50percent aq. NaOH / 40 h / Ambient temperature

3: NaOH / methanol / 3 h / Ambient temperature

4: pyridine / methanol

With pyridine; sodium hydroxide; DBN; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; methanol;

DOI:10.1021/jo00006a015

upstream raw materials:

1,1-Dichloro-1a,2,3,7b-tetrahydro-1H-cyclopropanaphthalen-2-ol

benzoyl chloride

1,4-dihydronaphthalene

(2α,3β)-2-Hydroxy-3-bromo-1,2,3,4-tetrahydronaphthalene

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