rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester
• CAS No.: 122444-31-9
• Molecular Formula: C₂₈H₃₄O₈
• Molecular Weight: 498.573
• Mol file: 122444-31-9.mol

Synonyms:rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester

Chemical Property of rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester

There total 5 articles about rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic 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: 78.8%

1-(2,4-dihydroxy-3-propylphenyl)ethanone (40786-69-4) + rac-5-acetyl-6-<(5-bromopentyl)oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester (122443-94-1) → rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester (122444-31-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; acetone; for 5.5h; Heating;

DOI:10.1021/jm00128a028

Reference yield:

diethyl 6-(benzyloxy)-3-hydroxybenzofuran-2,2(3H)-dicarboxylate (122443-91-8) → rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester (122444-31-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 85.6 percent / H₂, conc. H₂SO₄ / 10percent Pd/C / acetic acid / 2280 Torr / Ambient temperature

2: 9.6 g / BF₃*Et₂O, Ac₂O / 19 h / 120 °C

3: BF₃*Et₂O / 17 h / Heating

4: 67.6 percent / K₂CO₃ / 18-crown-6 / acetonitrile / 22 h / Heating

5: 78.8 percent / K₂CO₃ / acetone; dimethylformamide / 5.5 h / Heating

With sulfuric acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; potassium carbonate; palladium on activated charcoal; 18-crown-6 ether; In acetic acid; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jm00128a028

Reference yield:

5-Acetyl-6-hydroxy-2,3-dihydro-benzofuran-2-carboxylic acid (122444-30-8) → rac-5-acetyl-6-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester (122444-31-9)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*Et₂O / 17 h / Heating

2: 67.6 percent / K₂CO₃ / 18-crown-6 / acetonitrile / 22 h / Heating

3: 78.8 percent / K₂CO₃ / acetone; dimethylformamide / 5.5 h / Heating

With boron trifluoride diethyl etherate; potassium carbonate; 18-crown-6 ether; In N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jm00128a028

upstream raw materials:

1-(2,4-dihydroxy-3-propylphenyl)ethanone

rac-5-acetyl-6-<(5-bromopentyl)oxy>-2,3-dihydrobenzofuran-2-carboxylic acid methyl ester

diethyl 6-(benzyloxy)-3-hydroxybenzofuran-2,2(3H)-dicarboxylate

5-Acetyl-6-hydroxy-2,3-dihydro-benzofuran-2-carboxylic acid