5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane]

Base Information

• Chemical Name: 5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane]
• CAS No.: 432036-80-1
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.34
• Mol file: 432036-80-1.mol

Synonyms:5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane]

Chemical Property of 5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane]

There total 8 articles about 5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane] 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: 85.0%

5-benzyloxy-1,2,3,4-tetrahydro-2-oxonaphthalene (432036-79-8) → 5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane] (432036-80-1)

Guidance literature:

5-benzyloxy-1,2,3,4-tetrahydro-2-oxonaphthalene; With potassium tert-butylate; trimethylsulfoxonium iodide; In toluene; at 20 - 80 ℃; for 2h; Large scale;

With alumina; In ethyl acetate; Large scale;

DOI:10.1021/op3003085

Reference yield:

5-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-ol (211805-74-2) → 5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane] (432036-80-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydrogensulfate / toluene / 1 h / Reflux; Large scale

2.1: 3-chloro-benzenecarboperoxoic acid / toluene / 1.5 h / 5 - 30 °C / Large scale

3.1: toluene-4-sulfonic acid / toluene / 1 h / 85 - 90 °C / Large scale

4.1: trimethylsulfoxonium iodide; potassium tert-butylate / toluene / 2 h / 20 - 80 °C / Large scale

4.2: Large scale

With potassium hydrogensulfate; potassium tert-butylate; trimethylsulfoxonium iodide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In toluene; 3.1: |Meinwald Rearrangement;

DOI:10.1021/op3003085

Reference yield:

5-benzyloxy-3,4-dihydronaphthalene (432036-78-7) → 5-benzyloxy-1,23,4-tetrahydrospiro[naphthalene-2,2'-oxirane] (432036-80-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / toluene / 1.5 h / 5 - 30 °C / Large scale

2.1: toluene-4-sulfonic acid / toluene / 1 h / 85 - 90 °C / Large scale

3.1: trimethylsulfoxonium iodide; potassium tert-butylate / toluene / 2 h / 20 - 80 °C / Large scale

3.2: Large scale

With potassium tert-butylate; trimethylsulfoxonium iodide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In toluene; 2.1: |Meinwald Rearrangement;

DOI:10.1021/op3003085

upstream raw materials:

4-benzyloxy-1a,2,3,7b-tetrahydronaphtho[1,2-b]oxirane

5-benzyloxy-1,2,3,4-tetrahydro-2-oxonaphthalene

5-Hydroxy-1-tetralone

5-benzyloxy-1,2,3,4-tetrahydro-naphthalen-1-one

Downstream raw materials:

(5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methanol

(-)-(1S,4R)-camphanic acid [(5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester

(-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester

(-)-(1S,4R)-camphanic acid [((2S)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester