Methyl (4Z)-5-chloro-3-hydroxy-2-methylidene-5-(4-methylphenyl)pent-4-enoate

Base Information

• Chemical Name: Methyl (4Z)-5-chloro-3-hydroxy-2-methylidene-5-(4-methylphenyl)pent-4-enoate
• CAS No.: 1219452-57-9
• Molecular Formula: C₁₄H₁₅ClO₃
• Molecular Weight: 266.724
• DSSTox Substance ID: DTXSID70705010

Synonyms:1219452-57-9;DTXSID70705010;Methyl (4Z)-5-chloro-3-hydroxy-2-methylidene-5-(4-methylphenyl)pent-4-enoate

Chemical Property of Methyl (4Z)-5-chloro-3-hydroxy-2-methylidene-5-(4-methylphenyl)pent-4-enoate

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 266.0709720
• Heavy Atom Count: 18
• Complexity: 341

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=CC(C(=C)C(=O)OC)O)Cl
• Isomeric SMILES: CC1=CC=C(C=C1)/C(=C/C(C(=C)C(=O)OC)O)/Cl

Technology Process of Methyl (4Z)-5-chloro-3-hydroxy-2-methylidene-5-(4-methylphenyl)pent-4-enoate

There total 4 articles about Methyl (4Z)-5-chloro-3-hydroxy-2-methylidene-5-(4-methylphenyl)pent-4-enoate 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: 88.0%

(Z)-3-chloro-3-(p-tolyl)acrylaldehyde (40808-08-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (Z)-methyl 5-chloro-3-hydroxy-2-methylene-5-p-tolylpent-4-enoate (1219452-57-9)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; at 50 ℃; for 3h; Neat (no solvent); Sonication;

DOI:10.1080/00397910903262187

Reference yield: 47.0%

(Z)-3-chloro-3-(p-tolyl)acrylaldehyde (40808-08-0) + toluene-4-sulfonamide (70-55-3) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (Z)-methyl 5-chloro-3-hydroxy-2-methylene-5-p-tolylpent-4-enoate (1219452-57-9) + (Z)-methyl 5-chloro-2-methylene-3-(4-tolylsulfonamido)-5-(4-tolyl)pent-4-enoate (1254255-16-7)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; aluminum (III) chloride; at 20 ℃; for 1h; Neat (no solvent);

DOI:10.3184/030823410X12627215361201

Reference yield: 45.0%

benzenesulfonamide (98-10-2) + (Z)-3-chloro-3-(p-tolyl)acrylaldehyde (40808-08-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → (Z)-methyl 5-chloro-3-hydroxy-2-methylene-5-p-tolylpent-4-enoate (1219452-57-9) + (Z)-methyl 5-chloro-2-methylene-3-(phenylsulfonamido)-5-(4-tolyl)pent-4-enoate (1254255-18-9)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; aluminum (III) chloride; at 20 ℃; for 24h; Neat (no solvent);

DOI:10.3184/030823410X12627215361201

upstream raw materials:

benzenesulfonamide

(Z)-3-chloro-3-(p-tolyl)acrylaldehyde

acrylic acid methyl ester

toluene-4-sulfonamide

Downstream raw materials:

methyl (2Z,4Z)-2-(bromomethyl)-5-chloro-5-p-tolylpenta-2,4-dienoate

methyl 6-p-tolyl-2H-pyran-3-carboxylate

(2Z,4Z)-methyl 5-chloro-2-(chloromethyl)-5-(p-tolyl)penta-2,4-dienoate

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