1,2-Cyclooctanedione, 3-(phenylmethoxy)-

Base Information

• Chemical Name: 1,2-Cyclooctanedione, 3-(phenylmethoxy)-
• CAS No.: 664987-30-8
• Molecular Formula: C15H18O3
• Molecular Weight: 246.306
• Mol file: 664987-30-8.mol

Synonyms:

Chemical Property of 1,2-Cyclooctanedione, 3-(phenylmethoxy)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Cyclooctanedione, 3-(phenylmethoxy)-

There total 5 articles about 1,2-Cyclooctanedione, 3-(phenylmethoxy)- 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: 99%

trans-2-benzyloxy-8-hydroxycyclooctanone → 3-benzyloxy-1,2-cyclooctanedione (664987-30-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo0358675

Reference yield:

(5Z)-2-hydroxycycloocten-1-one (56879-17-5) → 3-benzyloxy-1,2-cyclooctanedione (664987-30-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / hydrogen / palladium on carbon / ethanol / 3.17 h / 760 Torr

2.1: 82 percent / Tf₂O / diethyl ether

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C

3.2: chlorotrimethylsilane / tetrahydrofuran / 20 °C

3.3: 50 percent / oxone; NaHCO₃ / H₂O; acetone / 0 - 20 °C

4.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With trifluoromethylsulfonic anhydride; hydrogen; Dess-Martin periodane; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jo0358675

Reference yield:

2-hydroxycylooctanone (496-82-2) → 3-benzyloxy-1,2-cyclooctanedione (664987-30-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CF₃SO₃H / diethyl ether

2.1: LHMDS / tetrahydrofuran / -78 °C

2.2: 50 percent / TMSCl; oxone; aq. NaHCO₃ / acetone

3.1: 99 percent / Dess-Martin periodinane

With trifluorormethanesulfonic acid; Dess-Martin periodane; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether;

upstream raw materials:

2-hydroxycylooctanone

O-benzyl 2,2,2-trichloroacetimidate

2-(benzyloxy)cyclooctanone

(5Z)-2-hydroxycycloocten-1-one

Downstream raw materials:

cyclooctane-1,2,3-triol

cyclooctane-1,2,3-triol

(1S,2R)-Cyclooctane-1,2,3-triol

cis-2,3-dihydroxycyclooctanone

Refernces

• 1、 Paquette, Leo A.,Hartung, Ryan. "Chemical consequences of the ground-state conformations of cyclooctyl rings. Examples of reactivity differences in α-hydroxy and α,α′-dihydroxy eight-membered cyclic ketones". . p. 1201 - 1208. Retrieved 2007/10/03.