cis-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin

Base Information

• Chemical Name: cis-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin
• CAS No.: 81109-38-8
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.295
• Mol file: 81109-38-8.mol

Synonyms:

Chemical Property of cis-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin

There total 12 articles about cis-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin 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: 49.0%

trans-and-3,4-dihydro-4-hydroxyacetyl-8-methoxy-3-phenylisocoumarin (81109-37-7,81109-39-9) → 3-hydroxy-α-hydroxyacetyl-2-stilbenecarboxylic acid (81109-42-4) + trans-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin (81109-38-8,81109-40-2)

Guidance literature:

With boron tribromide; In dichloromethane; for 5h; ice-cooled;

DOI:10.1248/cpb.29.3486

Reference yield: 26.0%

cis-3,4-dihydro-4-hydroxyacetyl-8-methoxy-3-phenylisocoumarin (81109-37-7,81109-39-9) → cis-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin (81109-38-8,81109-40-2)

Guidance literature:

With boron tribromide; In dichloromethane; for 0.0833333h; ice-cooled;

DOI:10.1248/cpb.29.3486

Reference yield:

8-methoxyhomophthalic anhydride (74794-52-8) → trans-3,4-dihydro-8-hydroxy-4-hydroxyacetyl-3-phenylisocoumarin (81109-38-8,81109-40-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / Na₂CO₃ / benzene / 15 h / Ambient temperature

2: SOCl₂ / 1.5 h / Heating

3: 74 percent / acetone

4: 83 percent / 10 percent H₂SO₄ / dioxane / 3.5 h / 40 °C

5: 25 percent / BBr₃ / CH₂Cl₂ / 0.08 h / ice-cooled

With thionyl chloride; sulfuric acid; boron tribromide; sodium carbonate; In 1,4-dioxane; dichloromethane; acetone; benzene;

DOI:10.1248/cpb.29.3486

upstream raw materials:

trans-and-3,4-dihydro-4-hydroxyacetyl-8-methoxy-3-phenylisocoumarin

8-methoxyhomophthalic anhydride

benzaldehyde

(3S,4S)-8-Methoxy-1-oxo-3-phenyl-isochroman-4-carboxylic acid

Refernces