2,2-Dimethyl-5-hexenoic acid

Base Information

• Chemical Name: 2,2-Dimethyl-5-hexenoic acid
• CAS No.: 58203-68-2
• Molecular Formula: C8H14 O2
• Molecular Weight: 142.198
• DSSTox Substance ID: DTXSID50441969
• Nikkaji Number: J1.014.815D
• Wikidata: Q82258994
• Mol file: 58203-68-2.mol

Synonyms:2,2-DIMETHYL-5-HEXENOIC ACID;58203-68-2;2,2-dimethylhex-5-enoic Acid;MFCD02258574;5-Hexenoic acid, 2,2-dimethyl-;2,2-dimethylhex-5-enoicAcid;SCHEMBL2292176;DTXSID50441969;LUOVXOGESOTATJ-UHFFFAOYSA-N;AC8558;AKOS006277449;SY262269;FT-0691338;EN300-206113;F2147-6455

Chemical Property of 2,2-Dimethyl-5-hexenoic acid

Chemical Property:

• PSA: 37.30000
• LogP: 2.06340
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

2,2-DIMETHYL-5-HEXENOICACID 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CCC=C)C(=O)O

Technology Process of 2,2-Dimethyl-5-hexenoic acid

There total 8 articles about 2,2-Dimethyl-5-hexenoic acid 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: 97.0%

ethyl 1-but-3-en-1-ylcyclohexanecarboxylate (73062-97-2) → 2,2-dimethylhex-5-enoic acid (58203-68-2)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 40 ℃; for 18h;

DOI:10.1002/ejoc.201301529

Reference yield: 91.0%

methyl 2,2-dimethyl-5-hexenoate (252206-21-6) → 2,2-dimethylhex-5-enoic acid (58203-68-2)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; at 25 - 40 ℃; for 2h;

DOI:10.1002/chem.200400460

Reference yield:

2,2-dimethyl-5-trimethylstannylcyclohexanone → bis(trimethyltin)oxide (1692-18-8) + 2,2-dimethylhex-5-enoic acid (58203-68-2)

Guidance literature:

With dihydrogen peroxide; potassium acetate; acetic acid; In water; at 20 ℃; for 168h;

DOI:10.1039/a804427i

upstream raw materials:

5-chloro-5-methyl-1-hexene

carbon dioxide

pivalolactone

methyl 2,2-dimethyl-5-hexenoate

Downstream raw materials:

2,2-dimethyl-4-hydroxyhexanoic acid γ-lactone

tetrahydro-3,3,6-trimethyl-2H-pyran-2-one

(1,1-dimethylpent-4-enyl)carbamic acid benzyl ester

(±)-2,2,6,6-tetramethyl-5-[(triisopropylsilyl)ethynyl]dec-9-en-3-yn-5-yl 2,3,4,5,6-pentafluorobenzoate

Refernces

• 1、 Maddocks, Christopher J.,Ermanis, Kristaps,Clarke, Paul A.. "Asymmetric "clip-Cycle" Synthesis of Pyrrolidines and Spiropyrrolidines". supporting information. p. 8116 - 8121. Retrieved 2020/11/02.
• 2、 Mueller, I.-E. Sophie,Bernet, Bruno,Dengiz, Cagatay,Schweizer, W. Bernd,Diederich, Francois. "Towards stapling of helical alleno-acetylene oligomers - Synthesis of an enantiopure bis(ethynylvinylidene)-substituted cyclohexadeca-1,3,9,11-tetrayne". supporting information. p. 941 - 953. Retrieved 2014/03/21.