Diethyl 4-hydroxyisophthalate

Base Information

• Chemical Name: Diethyl 4-hydroxyisophthalate
• CAS No.: 5985-25-1
• Molecular Formula: C12H14O5
• Molecular Weight: 238.24
• NSC Number: 84110
• UNII: L907M9989M
• DSSTox Substance ID: DTXSID90208573
• Wikidata: Q27282849
• Mol file: 5985-25-1.mol

Synonyms:Diethyl 4-hydroxyisophthalate;5985-25-1;Isophthalic acid, 4-hydroxy-, diethyl ester;NSC-84110;UNII-L907M9989M;4-Hydroxyisophthalic acid diethyl ester [MI];L907M9989M;1,3-Benzenedicarboxylic acid, 4-hydroxy-, diethyl ester;1,3-Benzenedicarboxylic acid, 4-hydroxy-, 1,3-diethyl ester;4-Hydroxyisophthalic acid, diethyl ester;1, 4-hydroxy-, diethyl ester;SCHEMBL10570974;DTXSID90208573;NSC84110;Q27282849

Chemical Property of Diethyl 4-hydroxyisophthalate

Chemical Property:

• Vapor Pressure: 6.64E-05mmHg at 25°C
• Boiling Point: 334.3°C at 760 mmHg
• Flash Point: 123°C
• Density: 1.211g/cm³
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 238.08412354
• Heavy Atom Count: 17
• Complexity: 276

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Diethyl 4-hydroxyisophthalate

There total 10 articles about Diethyl 4-hydroxyisophthalate 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: 95.0%

ethanol (64-17-5) + 4-hydroxyisophthalic acid (636-46-4) → 4-hydroxy-1,3-benzenedicarboxylic acid diethyl ester (5985-25-1)

Guidance literature:

With thionyl chloride; for 1h; Cooling with ice; Reflux;

Reference yield: 92.0%

ethyl 2-[(dimethylamino)methylene]-3-oxobutanoate (134653-70-6,51145-57-4) → 4-hydroxy-1,3-benzenedicarboxylic acid diethyl ester (5985-25-1)

Guidance literature:

With tetraethoxy orthosilicate; lithium hydride; In 1,2-dimethoxyethane; for 5h; chemoselective reaction; Reflux;

DOI:10.1021/acs.joc.9b00623

Reference yield: 30.0%

(S)-ethyl 3-amino-6-hydroxylhexanoate (356517-57-2) + 4-(trifluoromethanesulfonyloxy)isophthalic acid diethyl ester (489426-11-1) → 4-hydroxy-1,3-benzenedicarboxylic acid diethyl ester (5985-25-1) + 4-((S)-1-Ethoxycarbonylmethyl-4-hydroxy-butylamino)-isophthalic acid diethyl ester

Guidance literature:

With triethylamine; In acetonitrile; Heating;

DOI:10.1021/jo026125z

upstream raw materials:

ethanol

4-hydroxyisophthalic acid

ethyl acetoacetate

1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde

Downstream raw materials:

(2'S)-4-[5'-(tert-butyldimethylsilanyloxy)-1'-ethoxycarbonylpent-2'-yl]aminoisophthalic acid diethyl ester

4-(trifluoromethanesulfonyloxy)isophthalic acid diethyl ester

4-hydroxy-5-nitro-isophthalic acid diethyl ester

4-hydroxyisophthalic acid

Refernces

• 1、 -. "4-Hydroxyl-1,3 di-phthalate derivatives and preparation and application thereof". Paragraph 0035; 0036. . Retrieved 2017/01/02.
• 2、 Hirota, Kosaku,Kitade, Yukio,Senda, Shigeo. "Pyrimidine Derivatives and Related Compounds. 39. A Novel Cycloaromatization Reaction of 5-Formyl-1,3-dimethyluracil with Three-Carbon Nucleophiles. Synthesis of Substituted 4-Hydroxybenzoates". . p. 3949 - 3953. Retrieved 2007/10/02.