4-O-Demethylbarbatic acid

Base Information

• Chemical Name: 4-O-Demethylbarbatic acid
• CAS No.: 20372-89-8
• Molecular Formula: C₁₈H₁₈O₇
• Molecular Weight: 346.337
• UNII: X537335JTZ
• Nikkaji Number: J94.606K
• Wikidata: Q104967306
• Mol file: 20372-89-8.mol

Synonyms:4-O-Demethylbarbatic acid;20372-89-8;4-O-Demethyl-barbatic acid;Demethylbarbatic acid, 4-o-;Barbatic acid, 4-O-demethyl-;X537335JTZ;UNII-X537335JTZ;Benzoic acid, 2,4-dihydroxy-3,6-dimethyl-, 4-carboxy-3-hydroxy-2,5-dimethylphenyl ester;4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid;beta-Resorcylic acid, 3,6-dimethyl-, 4-(3,6-dimethyl-beta-resorcylate);.BETA.-RESORCYLIC ACID, 3,6-DIMETHYL-, 4-(3,6-DIMETHYL-.BETA.-RESORCYLATE)

Chemical Property of 4-O-Demethylbarbatic acid

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 346.10525291
• Heavy Atom Count: 25
• Complexity: 508

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)O)O)C)O)C)O

Technology Process of 4-O-Demethylbarbatic acid

There total 12 articles about 4-O-Demethylbarbatic 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: 91.0%

benzyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate (56410-43-6) → 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid (20372-89-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate;

DOI:10.1016/S0223-5234(99)00132-4

Reference yield:

ethyl 2,4-dihydroxy-3,6-dimethylbenzoate (31581-32-5) → 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid (20372-89-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / K₂CO₃ / acetone / 24 h / Heating

2: 84 percent / aq. KOH / dimethylsulfoxide / Heating

3: 78 percent / (CF₃-CO)2O / toluene / 20 °C

4: 91 percent / H₂; 10 percent Pd/C / ethyl acetate

With potassium hydroxide; palladium on activated charcoal; hydrogen; potassium carbonate; trifluoroacetic anhydride; In dimethyl sulfoxide; ethyl acetate; acetone; toluene; 1: Alkylation / 2: Hydrolysis / 3: Esterification / 4: Hydrogenolysis;

DOI:10.1016/S0223-5234(99)00132-4

Reference yield:

ethyl 4-benzyloxy-2-hydroxy-3,6-dimethylbenzoate (56410-31-2) → 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoic acid (20372-89-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / aq. KOH / dimethylsulfoxide / Heating

2: 78 percent / (CF₃-CO)2O / toluene / 20 °C

3: 91 percent / H₂; 10 percent Pd/C / ethyl acetate

With potassium hydroxide; palladium on activated charcoal; hydrogen; trifluoroacetic anhydride; In dimethyl sulfoxide; ethyl acetate; toluene; 1: Hydrolysis / 2: Esterification / 3: Hydrogenolysis;

DOI:10.1016/S0223-5234(99)00132-4

upstream raw materials:

benzyl 4-(4-benzyloxy-2-hydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate

ethyl 2,4-dihydroxy-3,6-dimethylbenzoate

4-benzyloxy-2-hydroxy-3,6-dimethylbenzoic acid

ethyl 4-benzyloxy-2-hydroxy-3,6-dimethylbenzoate

Downstream raw materials:

2,4-dihydroxy-3,6-dimethylbenzoic acid

2,5-dimethyl-1,3-benzenediol

methyl 4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-hydroxy-3,6-dimethylbenzoate

Refernces