5-Methyl-2-(1-methylethenyl)-4-hexenoic acid

Base Information

• Chemical Name: 5-Methyl-2-(1-methylethenyl)-4-hexenoic acid
• CAS No.: 497-67-6
• Molecular Formula: C10H16O2
• Molecular Weight: 168.236
• DSSTox Substance ID: DTXSID60964351
• Nikkaji Number: J1.932.507E
• Mol file: 497-67-6.mol

Synonyms:5-Methyl-2-(1-methylethenyl)-4-hexenoic acid;497-67-6;5-methyl-2-prop-1-en-2-ylhex-4-enoic acid;5-Methyl-2-(prop-1-en-2-yl)hex-4-enoic acid;2-Isopropenyl-5-methyl-4-hexenoic acid;4-Hexenoic acid, 5-methyl-2-(1-methylethenyl)-;starbld0029671;SCHEMBL3359833;DTXSID60964351;NNVQOMNUZSZZAL-UHFFFAOYSA-N

Chemical Property of 5-Methyl-2-(1-methylethenyl)-4-hexenoic acid

Chemical Property:

• Vapor Pressure: 0.00167mmHg at 25°C
• Boiling Point: 272.6°C at 760 mmHg
• Flash Point: 169.8°C
• Density: 0.95g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 210

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 5-Methyl-2-(1-methylethenyl)-4-hexenoic acid

There total 14 articles about 5-Methyl-2-(1-methylethenyl)-4-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: 93.0%

(±)-ethyl 5-methyl-2-(prop-1-en-2-yl)hex-4-enoate (1845-54-1) → 2-(1-methylethenyl)-5-methyl-4-hexenoic acid (497-67-6)

Guidance literature:

With sodium hydroxide; In ethanol; for 8h; Heating;

Reference yield: 75.0%

5-Methyl-2-(1'-methylethyliden)-4-hexensaeure-ethylester (3304-29-8) → 2-(1-methylethenyl)-5-methyl-4-hexenoic acid (497-67-6)

Guidance literature:

With potassium hydroxide; In ethanol; for 6h; Heating;

DOI:10.1021/jo00129a030

Reference yield:

3-Methylbutenoic acid (541-47-9) + prenyl bromide (870-63-3) → (E)-geranic acid (4698-08-2) + 2-(1-methylethenyl)-5-methyl-4-hexenoic acid (497-67-6)

Guidance literature:

3-Methylbutenoic acid; With lithium diethylamide; In tetrahydrofuran; at 0 ℃; for 0.5h;

prenyl bromide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(03)01028-7

upstream raw materials:

isopropenyl-(3-methyl-but-2-enyl)-malonic acid diethyl ester

(±)-ethyl 5-methyl-2-(prop-1-en-2-yl)hex-4-enoate

5-Methyl-2-(1'-methylethyliden)-4-hexensaeure-ethylester

3-Methylbutenoic acid

Downstream raw materials:

(2,4,4-trimethyl-1-cyclohexen-1-yl)carboxylic acid

3-terpinolenone

(2,4,4-trimethyl-1-cyclohexen-1-yl)methanol

1-(bromomethyl)-2,4,4-trimethyl-1-cyclohexene

Refernces

• 1、 -. "METHOD FOR PRODUCING (E)-2-ISOPROPYL-5-METHYL-2,4-HEXADIENYL ACETATE". Paragraph 0078-0079. . Retrieved 2015/05/05.
• 2、 Froehner, Wolfgang,Reddy, Kethiri R.,Knoelker, Hans-Joachim. "Transition metals in organic synthesis, Part 98.1 Transition metal mediated total synthesis of the potent neuronal cell protecting alkaloid (±)-lavanduquinocin". . p. 330 - 342. Retrieved 2013/09/24.