Ethyl 4-hydroxy-3-methylbenzofuran-2-carboxylate

Base Information

• Chemical Name: Ethyl 4-hydroxy-3-methylbenzofuran-2-carboxylate
• CAS No.: 3781-69-9
• Molecular Formula: C12H12 O4
• Molecular Weight: 220.22
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID40353704
• Nikkaji Number: J819.322C
• Wikidata: Q82131428
• ChEMBL ID: CHEMBL1490774
• Mol file: 3781-69-9.mol

Synonyms:3781-69-9;ETHYL 4-HYDROXY-3-METHYLBENZOFURAN-2-CARBOXYLATE;ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate;CBMicro_024542;Oprea1_494631;MLS000530573;SCHEMBL3610633;4-Hydroxy-3-methyl-benzofuran-2-carbonsaeure-aethylester;CHEMBL1490774;DTXSID40353704;NBTXBAOGAXOKEV-UHFFFAOYSA-N;4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester;HMS2407E07;2-Benzofurancarboxylic acid, 4-hydroxy-3-methyl-, ethyl ester;AC6036;CCG-14173;MFCD00770214;STK279759;AKOS001629075;SMR000135552;SY045669;2-carbethoxy-3-methyl-4-hydroxybenzofuran;BIM-0024596.P001;CS-0255280;FT-0761417;UNM000006360602;EN300-298183;ethyl 3-methyl-4-hydroxybenzofuran-2-carboxylate;ethyl-4-hydroxy-3-methylbenzofuran-2-carboxylate;A924215;AJ-292/43410833;SR-01000453589;SR-01000453589-1

Chemical Property of Ethyl 4-hydroxy-3-methylbenzofuran-2-carboxylate

Chemical Property:

• PSA: 59.67000
• LogP: 2.62350
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 220.07355886
• Heavy Atom Count: 16
• Complexity: 266

Purity/Quality:

97% ^*data from raw suppliers

ETHYL-4-HYDROXY-3-METHYL-1-BENZOFURAN-2-CARBOXYLATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=C(C=CC=C2O1)O)C

Technology Process of Ethyl 4-hydroxy-3-methylbenzofuran-2-carboxylate

There total 11 articles about Ethyl 4-hydroxy-3-methylbenzofuran-2-carboxylate 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: 98.0%

3-methyl-4-oxo-4,5,6,7-tetrahydrofuran-2-carboxylic acid ethyl ester (108993-84-6) → 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (3781-69-9)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; water; Heating;

DOI:10.1002/jhet.5570400305

Reference yield: 46.0%

ethyl 2-(2-acetyl-3-hydroxyphenoxy)acetate (6769-65-9) → 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (3781-69-9)

Guidance literature:

With sodium ethanolate; In ethanol; at -18 - 20 ℃; for 18h; Inert atmosphere;

Reference yield:

2,6-dihydroxylacetophenone (699-83-2) → 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (3781-69-9)

Guidance literature:

Multi-step reaction with 2 steps

1: K₂CO₃ / acetone / 15 h / 60 °C

2: NaOEt / ethanol / 20 h / 0 °C

With sodium ethanolate; potassium carbonate; In ethanol; acetone;

DOI:10.1016/S0960-894X(01)00319-5

upstream raw materials:

ethyl 2-(2-acetyl-3-hydroxyphenoxy)acetate

2,2,2-trichloro-1-(4-hydroxy-3-methyl-benzofuran-2-yl)-ethanone

ethanol

3-methyl-4-oxo-4,5,6,7-tetrahydrofuran-2-carboxylic acid ethyl ester

Downstream raw materials:

2-carbethoxy-3-methyl-4-acetoxybenzofuran

ethyl 5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-carboxylate

methyl N-({4'-[(4-ethyl-3-methyl-1-benzofuran-2-yl)methoxy]-1,1'-biphenyl-4-yl}sulfonyl)-L-valinate

methyl N-[(4'-{[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methoxy}-1,1'-biphenyl-4-yl)sulfonyl]-L-valinate