Sulfuric Acid → Methyl 5-Iodosalicylate

HRID 368296

Reaktionsgleichung

Reaktionsgleichung von HRID 368296
[I:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH:12](OC)(OC)OC.S(=O)(=O)(O)O>CO>[CH3:12][O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([I:1])[CH:10]=1)[OH:11]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 83885-Iodosalicylic acidHCID 9005Trimethyl orthoformate

Produkt 1

HCID 248910Methyl 5-Iodosalicylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

5-Iodosalicylic acid (Aldrich Chemical Company, Milwaukee, Wis.) is converted to the methyl ester by reaction with methanol, trimethyl orthoformate and sulfuric acid. The 5-iodosalicylic acid methyl ester thus obtained is reacted with (trimethylsilyl)acetylene (Aldrich Chemical Company, Milwaukee, Wis.) in the presence of palladium. The trimethylsilyl group is removed and two equivalents of the resultant 5-acetylenylsalicylic acid methyl ester is reacted with 4,4'-dibromobiphenyl (Aldrich Chemical Company, Milwaukee, Wis.) in the presence of palladium as above. The resultant alkynyl analogue of Chrysamine G, 4,4'-bis(3-methoxycarbonyl-4-hydroxyphenylacetylenyl)-biphenyl is prepared by hydrolysis of the ester as described above.

Quellen und Nachweise

ORD-Eintrag
ord-41e292c8f77545939f90e40c8d409a74
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133259

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