2151-16-8

Basic information

• Product Name: 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester
• Synonyms: 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester;2-(3,5-Dichloro-2,6-dihydroxy-4-methylbenzoyl)-5-hydroxy-3-methoxybenzoic acid methyl ester;2-[2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl]-3-methoxy-5-hydroxybenzoic acid methyl ester;Dihydrogeodin
• CAS NO: 2151-16-8
• Molecular Formula: C₁₇H₁₄Cl₂O₇
• Molecular Weight: 401.19
• Mol File: 2151-16-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester(2151-16-8)
• EPA Substance Registry System: 2-(2,6-Dihydroxy-3,5-dichloro-4-methylbenzoyl)-3-methoxy-5-hydroxybenzoic acid methyl ester(2151-16-8)

Safety Data

• Hazardous Substances Data: 2151-16-8(Hazardous Substances Data)

Upstream product

• 504-15-4 orcinol 
• 261958-58-1 4-{[2-benzyloxymethyl-6-methoxy-4-(methoxymethoxy)phenyl]hydroxymethyl}-3,5-bis(methoxymethoxy)-2,6-dichlorotoluene 
• 261958-59-2 2'-benzyloxymethyl-6'-methoxy-2,4',6-tris(methoxymethoxy)-3,5-dichloro-4-methylbenzophenone 
• 261958-62-7 2-(3,5-dichloro-2,6-bis-methoxymethoxy-4-methyl-benzoyl)-3-methoxy-5-methoxymethoxy-benzoic acid 
• 261958-60-5 2-[2,6-bis(methoxymethoxy)-3,5-dichloro-4-methylbenzoyl]-3-methoxy-5-(methoxymethoxy)benzyl alcohol 
• 261958-61-6 2-[2,6-bis(methoxymethoxy)-3,5-dichloro-4-methylbenzoyl]-3-methoxy-5-(methoxymethoxy)benzaldehyde 
• 261958-54-7 2-benzyloxymethyl-4,6-bis(methoxymethoxy)benzaldehyde 
• 261958-53-6 2-benzyloxymethyl-4,6-bis(methoxymethoxy)bromobenzene 
• 261958-51-4 2-benzyloxymethyl-6-methoxy-4-(methoxymethoxy)benzaldehyde 
• 261958-56-9 2-benzyloxymethyl-6-hydroxy-4-(methoxymethoxy)benzaldehyde 
• 261958-52-5 3,5-bis(methoxymethoxy)-4-bromo-2,6-dichlorotoluene 
• 261958-55-8 2,4-dihydroxy-6-[(phenylmethoxy)methyl]-benzaldehyde 
• 261958-57-0 2-bromo-4,6-dichloro-5-methylbenzene-1,3-diol 
• 76280-59-6 methyl 3,5-bis(methoxymethoxy)benzoate 

Downstream Products

• 63992-61-0 4,6-dichloro-5-methylresorcinol 
• 89367-82-8 5-acetoxy-2-(2,6-diacetoxy-3,5-dichloro-4-methyl-benzoyl)-3-methoxy-benzoic acid methyl ester 
• 73855-53-5 3,5-dichloro-2,6-dihydroxy-4-methyl-benzoic acid 
• 500887-70-7 2-(3,5-dichloro-2,6-dimethoxy-4-methyl-benzoyl)-3,5-dimethoxy-benzoic acid methyl ester 
• 427-63-4 (+)-geodin 

Relevant articles and documents

Synthetic studies on Sch 202596, an antagonist of the galanin receptor subtype GalR1: An efficient synthesis of (±)-geodin, the spirocoumaranone part of Sch 202596

An efficient and facile synthesis of (±)-geodin [(±)-2] corresponding to the spirocoumaranone part of Sch 202596 (1) was accomplished in a convergent manner. The synthetic method features (i) a coupling reaction of the aryl aldehyde 6 with the aryl lithium 7 generated in situ from the aryl bromide 8 to deliver the highly substituted diaryl methanol 24 (6+7→24) and ii) oxidative spirocyclization reaction of the benzophenone 4 to construct the requisite spirocoumaranone skeleton [4→(±)-2] as the key steps. The aromatic segments 6 and 8 were prepared from commercially available methyl 3,5-dihydroxybenzoate (9) and 5-methylresorcinol (10), respectively.