5,5-Dimethylnorborna-2-ene

Base Information

• Chemical Name: 5,5-Dimethylnorborna-2-ene
• CAS No.: 497-28-9
• Molecular Formula: C9H14
• Molecular Weight: 122.21
• Mol file: 497-28-9.mol

Synonyms:

Chemical Property of 5,5-Dimethylnorborna-2-ene

Chemical Property:

• Melting Point: 27-28 °C
• Boiling Point: 140-141 °C(Press: 762 Torr)
• Density: 0.8678 g/cm3

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5-Dimethylnorborna-2-ene

There total 17 articles about 5,5-Dimethylnorborna-2-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: 8.0%

2-exo-norbornyl-p-toluenesulfonate → 5,5-Dimethyl-norborn-2-en (497-28-9,82077-11-0,82764-88-3,82764-90-7) + 6,6-dimethyl-exo-2-norbornanol (60322-71-6,63122-47-4,90645-88-8,91605-22-0,91605-24-2,111821-70-6)

Guidance literature:

With 1,4-dioxane; at 70 ℃; for 2h;

DOI:10.1002/hlca.19870700105

Reference yield:

(1S)-endo-2-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid (92007-58-4) → 5,5-dimethylbicyclo{2.2.1}hept-2-ene (497-28-9,82764-90-7)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether

2: (i) TsCl, Py, (ii) LiAlH₄, Et₂O

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1021/ja01480a012

Reference yield:

(+/-)-2-methyl-norborn-5-ene-2exo-carboxylic acid (32190-82-2) → 5,5-dimethylbicyclo{2.2.1}hept-2-ene (497-28-9,82764-90-7)

Guidance literature:

Multi-step reaction with 3 steps

2: LiAlH₄ / diethyl ether

3: (i) TsCl, Py, (ii) LiAlH₄, Et₂O

With lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1021/ja01480a012

upstream raw materials:

5,5-dimethyl-norbornan-2-ol

5-formyl-5-methylbicyclo[2.2.1]hept-2-ene

(1S-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-methanol

Toluene-4-sulfonic acid 2-methyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

Downstream raw materials:

6,6-dimethyl-2-norbornanone

2,6,6-trimethyl-endo-2-norbornyl p-nitrobenzoate

β-fenchocamphorone

(+/-)-phthalic acid mono-(5,5-dimethyl-[2exo]norbornyl ester)

Refernces

• 1、 Brown, Herbert C.,Ikegami, Shiro,Jagt, Dawid L. Vander. "Structural Effects in Solvolytic Reactions. 49. Steric Effects as a Major Factor in the Exo:Endo Rate Ratios for the Solvolysis of 2,7,7-Trimethyl- and 2,6,6-Trimethyl-2-norbornyl p-Nitrobenzoates". . p. 1165 - 1171. Retrieved 2007/10/02.
• 2、 Brown,Kawakami,Misumi. "Additions to bicyclic olefins. II. A convenient synthesis of apobornene and apocamphor.". . p. 1360 - 1363. Retrieved 2007/10/12.