2,4-Hexadienoic acid, 6-chloro-4-methyl-

Base Information

• Chemical Name: 2,4-Hexadienoic acid, 6-chloro-4-methyl-
• CAS No.: 104199-13-5
• Molecular Formula: C₇H₉ClO₂
• Molecular Weight: 160.6
• Mol file: 104199-13-5.mol

Synonyms:2,4-Hexadienoic acid, 6-chloro-4-methyl-;104199-13-5

Chemical Property of 2,4-Hexadienoic acid, 6-chloro-4-methyl-

Chemical Property:

• Vapor Pressure: 0.000123mmHg at 25°C
• Boiling Point: 311.5°C at 760 mmHg
• Flash Point: 142.2°C
• Density: 1.171g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 160.0291072
• Heavy Atom Count: 10
• Complexity: 170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCl)C=CC(=O)O
• Isomeric SMILES: C/C(=C\CCl)/C=C/C(=O)O

Technology Process of 2,4-Hexadienoic acid, 6-chloro-4-methyl-

There total 1 articles about 2,4-Hexadienoic acid, 6-chloro-4-methyl- 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:

(Z)-4-chloro-2-methyl-but-2-enal (3330-25-4) + diethyl <<(trimethylsilyl)oxy>carbonyl>methanephosphonate (66130-90-3) → (2E,4Z)-6-Chloro-4-methyl-hexa-2,4-dienoic acid (104199-13-5)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, 6 h, 2.) THF, hexane, 90 min;

DOI:10.1021/jo00373a004

Reference yield:

(2E,4Z)-6-Chloro-4-methyl-hexa-2,4-dienoic acid (104199-13-5) → (3aS,6aR,9aS,9bR)-4,7,9b-Trimethyl-3,3a,6,6a,9a,9b-hexahydro-benzo[de]chromene-2,9-dione (104199-03-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 50 percent / Zn, glacial acetic acid / Ambient temperature

2: 78 percent / benzene / 6 h / 60 °C

3: 92 percent / NaBH₄ / methanol / 0.5 h / -30 °C

4: 55 percent / tetrahydrofuran / 0.5 h / -40 °C

5: pyridine, diisopropylcarbodiimide / CH₂Cl₂ / 16.5 h

6: 61 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 36 h / Heating

With pyridine; sodium tetrahydroborate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diisopropyl-carbodiimide; zinc; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo00373a004

Reference yield:

(2E,4Z)-6-Chloro-4-methyl-hexa-2,4-dienoic acid (104199-13-5) → (3aS,6aR,9aR,9bR)-9b-Methoxymethyl-4,7-dimethyl-3,3a,6,6a,9a,9b-hexahydro-benzo[de]chromene-2,9-dione (104199-05-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / Zn, glacial acetic acid / Ambient temperature

2: 16 percent / CH₂Cl₂

3: 95 percent / NaBH₄ / methanol / 0.5 h / -30 °C

4: 71 percent / tetrahydrofuran / 0.5 h / -40 °C

5: 76 percent / pyridine, acetic anhydride / 1 h

With pyridine; sodium tetrahydroborate; acetic anhydride; acetic acid; zinc; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00373a004

upstream raw materials:

(Z)-4-chloro-2-methyl-but-2-enal

diethyl <<(trimethylsilyl)oxy>carbonyl>methanephosphonate

Downstream raw materials:

((1R,4aS,8S,8aS)-8-Hydroxy-2,5,8a-trimethyl-7-oxo-1,4,4a,7,8,8a-hexahydro-naphthalen-1-yl)-acetic acid

(3aS,6aS,9aR,9bS)-9-Methoxy-4,9b-dimethyl-3,3a,6,6a,9a,9b-hexahydro-benzo[de]chromene-2,7-dione

((1R,4aS,8S,8aS)-8-Hydroxy-8a-methoxymethyl-2,5-dimethyl-7-oxo-1,4,4a,7,8,8a-hexahydro-naphthalen-1-yl)-acetic acid

(3aS,6aS,9aR,9bS)-9-Methoxy-9b-methoxymethyl-4-methyl-3,3a,6,6a,9a,9b-hexahydro-benzo[de]chromene-2,7-dione