2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester

Base Information

• Chemical Name: 2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester
• CAS No.: 908339-23-1
• Molecular Formula: C₁₈H₁₈O₇
• Molecular Weight: 346.337
• Mol file: 908339-23-1.mol

Synonyms:2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester

Chemical Property of 2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester

There total 6 articles about 2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl 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: 85.0%

2,3-bis-benzyloxy-4-[4-(2-benzyloxy-phenyl)-1-hydroxy-3-oxo-butyl]-benzoic acid methyl ester (908339-22-0) → 2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester (908339-23-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 17h; under 760 Torr;

DOI:10.1021/ol061112j

Reference yield:

1-Benzyloxy-2-(2-nitro-ethyl)-benzene (908292-04-6) → 2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester (908339-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / phenyl isocyanate; triethylamine / benzene / 15 h / 60 °C

2: 61 percent / H₂; H₂O; boric acid / Raney Ni / methanol / 24 h / 20 °C / 760 Torr

3: 85 percent / H₂ / Pd/C / ethyl acetate / 17 h / 20 °C / 760 Torr

With water; hydrogen; boric acid; phenyl isocyanate; triethylamine; palladium on activated charcoal; nickel; In methanol; ethyl acetate; benzene;

DOI:10.1021/ol061112j

Reference yield:

4-formyl-2,3-dihydroxy-6-iodo-benzoic acid methyl ester → 2,3-dihydroxy-4-[1-hydroxy-4-(2-hydroxy-phenyl)-3-oxo-butyl]-benzoic acid methyl ester (908339-23-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 653 mg / K₂CO₃ / dimethylformamide / 20 °C

2.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / 0 °C

2.2: 83 percent / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

3.1: 71 percent / phenyl isocyanate; triethylamine / benzene / 15 h / 60 °C

4.1: 61 percent / H₂; H₂O; boric acid / Raney Ni / methanol / 24 h / 20 °C / 760 Torr

5.1: 85 percent / H₂ / Pd/C / ethyl acetate / 17 h / 20 °C / 760 Torr

With water; hydrogen; sec.-butyllithium; boric acid; potassium carbonate; phenyl isocyanate; triethylamine; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; cyclohexane; ethyl acetate; N,N-dimethyl-formamide; benzene; 2.2: Wittig reaction;

DOI:10.1021/ol061112j

upstream raw materials:

2,3-bis-benzyloxy-4-[4-(2-benzyloxy-phenyl)-1-hydroxy-3-oxo-butyl]-benzoic acid methyl ester

1-Benzyloxy-2-(2-nitro-ethyl)-benzene

2,3-bis-benzyloxy-4-formyl-6-iodo-benzoic acid methyl ester

2,3-bis-benzyloxy-6-iodo-4-vinyl-benzoic acid methyl ester