(4-Chloromethyl-phenoxy)-acetic acid ethyl ester

Base Information

• Chemical Name: (4-Chloromethyl-phenoxy)-acetic acid ethyl ester
• CAS No.: 80494-75-3
• Molecular Formula: C11H13 Cl O3
• Molecular Weight: 228.675
• DSSTox Substance ID: DTXSID00402247
• Wikidata: Q82205626
• Mol file: 80494-75-3.mol

Synonyms:80494-75-3;Ethyl 2-[4-(chloromethyl)phenoxy]acetate;(4-Chloromethyl-phenoxy)-acetic acid ethyl ester;Acetic acid,2-[4-(chloromethyl)phenoxy]-, ethyl ester;SCHEMBL7918868;DTXSID00402247;ethyl 4-chloromethylphenoxyacetate;QLVMJKOKSMMYTO-UHFFFAOYSA-N;AC-246;AKOS023249702;FT-0750921;(4-chloromethylphenoxy)acetic acid ethyl ester;(4-Chloromethyl-phenoxy)acetic acid ethyl ester

Chemical Property of (4-Chloromethyl-phenoxy)-acetic acid ethyl ester

Chemical Property:

• Vapor Pressure: 0.000329mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 319.9°C at 760 mmHg
• Flash Point: 129.7°C
• PSA: 35.53000
• Density: 1.177g/cm³
• LogP: 2.36730
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 228.0553220
• Heavy Atom Count: 15
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

(4-CHLOROMETHYL-PHENOXY)-ACETIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)COC1=CC=C(C=C1)CCl

Technology Process of (4-Chloromethyl-phenoxy)-acetic acid ethyl ester

There total 4 articles about (4-Chloromethyl-phenoxy)-acetic acid ethyl ester 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: 100.0%

ethyl 2-(4-hydroxymethylphenoxy)acetate (103258-64-6) → ethyl [p-(chloromethyl)phenoxy]acetate (80494-75-3)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 0.75h; Inert atmosphere;

DOI:10.1021/jm2002525

Reference yield:

(4-hydroxyphenyl)methanol (623-05-2) → ethyl [p-(chloromethyl)phenoxy]acetate (80494-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃

2: SOCl₂ / tetrahydrofuran

With thionyl chloride; potassium carbonate; In tetrahydrofuran;

DOI:10.1021/jm010086m

Reference yield:

4-hydroxy-benzoic acid (99-96-7) → ethyl [p-(chloromethyl)phenoxy]acetate (80494-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 - 20 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C

2.2: 6 h

3.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 °C / Reflux

With lithium aluminium tetrahydride; thionyl chloride; potassium carbonate; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bioorg.2020.104462

upstream raw materials:

ethyl 2-(4-hydroxymethylphenoxy)acetate

(4-hydroxyphenyl)methanol

4-hydroxy-benzoic acid

Downstream raw materials:

ethyl 4-<2-(phenylsulfonylamino)ethylthiomethyl>phenoxyacetate

(R)-2-(1-(4-(carboxymethoxy)benzyl)-1H-indole-6-carboxamido)pentanedioic acid

(R)-dimethyl 2-(1-(4-(2-ethoxy-2-oxoethoxy)benzyl)-1H-indole-6-carboxamido) pentanedioate

1-(4-(2-ethoxy-2-oxoethoxy)benzyl)-1H-indole-6-carboxylic acid

Refernces

• 1、 Lu?in, Tina Trdan,Toma?i?, Tihomir,Trontelj, Jurij,Mrhar, Ale?,Peterlin-Ma?i?, Lucija. "In vitro bioactivation of bazedoxifene and 2-(4-hydroxyphenyl)-3-methyl-1H- indol-5-ol in human liver microsomes". experimental part. p. 8 - 15. Retrieved 2012/07/28.
• 2、 Miller,Collini,Tran,Harris,Kharode,Marzolf,Moran,Henderson,Bender,Unwalla,Greenberger,Yardley,Abou-Gharbia,Lyttle,Komm. "Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens". . p. 1654 - 1657. Retrieved 2007/10/04.