robustic acid

Base Information

• Chemical Name: robustic acid
• CAS No.: 5307-59-5
• Molecular Formula: C22H20 O6
• Molecular Weight: 380.397
• Mol file: 5307-59-5.mol

Synonyms:2H,8H-Benzo[1,2-b:5,4-b']dipyran-2-one,4-hydroxy-5-methoxy-3-(p-methoxyphenyl)-8,8-dimethyl- (8CI);2H-1-Benzopyran-6-acrylic acid, b,7-dihydroxy-5-methoxy-a-(p-methoxyphenyl)-2,2-dimethyl-, d-lactone (7CI); Robustic acid

Chemical Property of robustic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 574.7°Cat760mmHg
• Flash Point: 203.1°C
• PSA: 78.13000
• Density: 1.303g/cm³
• LogP: 4.36700

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of robustic acid

There total 15 articles about robustic acid 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: 79.0%

4-methoxyphenyllead(IV) triacetate (18649-43-9) + 4-hydroxy-5-methoxy-8,8-dimethyl-2H,8H-benzo<1,2-b:5,4-b'>-dipyran-2-one (171021-68-4) → robustic acid (5307-59-5)

Guidance literature:

With pyridine; In chloroform; at 60 ℃; for 14h;

Reference yield:

3-Methylbutenoic acid (541-47-9) → robustic acid (5307-59-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) polyphosphoric acid, 2.) potassium carbonate / 1.) dioxane, 60 deg C, 3 h, 2.) acetone, reflux, 50 h

2: 64 percent / potassium carbonate / acetone / 2 h / Heating

3: 93 percent / potassium carbonate / acetone / 4 h / Heating

4: 70 percent / NaBH₄, PdCl₂ / tetrahydrofuran; H₂O / 1.5 h / 0 - 5 °C

5: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating

6: 95 percent / potassium carbonate / methanol / 1.5 h / Heating

7: 80 percent / sodium hydride / 0.5 h / 45 °C

8: 79 percent / pyridine / CHCl₃ / 14 h / 60 °C

With pyridine; sodium tetrahydroborate; PPA; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; palladium dichloride; In tetrahydrofuran; methanol; chloroform; water; acetone; toluene;

Reference yield:

6-acetyl-7-hydroxy-5-methoxy-2,2-dimethyl-2H-chromene (529-70-4) → robustic acid (5307-59-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / sodium hydride / 0.5 h / 45 °C

2: 79 percent / pyridine / CHCl₃ / 14 h / 60 °C

With pyridine; sodium hydride; In chloroform;

upstream raw materials:

8-iodo-4,5-dimethoxy-3-(4'-methoxyphenyl)-7-(1,1-dimethylprop-2-ynyloxy)coumarin

4-methoxyphenyllead(IV) triacetate

4-hydroxy-5-methoxy-8,8-dimethyl-2H,8H-benzo<1,2-b:5,4-b'>-dipyran-2-one

3-Methylbutenoic acid

Downstream raw materials:

robustic acid methyl ether

Refernces

• 1、 Ahluwalia, Vinod K.,Prakash, Chandra,Jolly, Ravinder S.. "Synthesis of Linear 3-Phenylpyranocoumarins: Synthesis of Robustin, Robustic Acid, and their Methyl Ethers". . p. 1697 - 1702. Retrieved 2007/10/02.