1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene

Base Information

• Chemical Name: 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene
• CAS No.: 216978-20-0
• Molecular Formula: C₁₈H₂₅ClO₃
• Molecular Weight: 324.848
• Mol file: 216978-20-0.mol

Synonyms:1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene

Chemical Property of 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene

There total 13 articles about 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene 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: 98.0%

1-(6-Chloro-1-hydroxyhex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene (189444-00-6) → 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene (216978-20-0)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 0 ℃;

Reference yield:

1-Formyl-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene (189443-99-0) → 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene (216978-20-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / n-BuLi / hexane; tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) -78 deg C, 30 min

2: 98 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1039/a805268i

Reference yield:

ethyl 2-acetyl-3-methylbut-2-enoate (35044-52-1) → 1-(6-Chloro-1-oxohex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene (216978-20-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / tetrahydrofuran / Ambient temperature

2: 92 percent / DIBAL-H / toluene / -60 °C

3: 93 percent / PTSA / benzene / 65 °C

4: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

5: 79 percent / BF₃*OEt₂ / toluene / 1.) -78 deg C, 5 min, 2.) -78 deg C, 10 h

6: 87 percent / CSA / benzene / 14 h / Ambient temperature

7: 94 percent / K₂CO₃ / methanol / 24 h / Ambient temperature

8: 88 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

9: 96 percent / n-BuLi / hexane; tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) -78 deg C, 30 min

10: 98 percent / tetra(n-propyl)ammonium perruthenate, NMO, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; benzene;

DOI:10.1039/a805268i

upstream raw materials:

1-(6-Chloro-1-hydroxyhex-2-ynyl)-5-(1,3-dioxolan-2-yl)-2,6,6-trimethylcyclohex-1-ene

ethyl 2-acetyl-3-methylbut-2-enoate

2-isopropenyl-3-methyl-crotonic acid

2-isopropenyl-3-methyl-crotonic acid methyl ester

Downstream raw materials:

5-Formyl-1-(6-chloro-1-oxohex-2-ynyl)-2,6,6-trimethylcyclohex-1-ene

1-(6-Chloro-1-oxohex-2-ynyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

1-(6-Iodo-1-oxohex-2-ynyl)-5-(1-oxoprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene

1-(6-Chloro-1-oxohex-2-ynyl)-5-(1-hydroxyprop-2-enyl)-2,6,6-trimethylcyclohex-1-ene