Sulfuric Acid → Methyl 5-Iodosalicylate

HRID 1952827Notes

Reaction equation

HRID 1952827 reaction equation
[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]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 83885-Iodosalicylic acidHCID 9005Trimethyl orthoformate

Product 1

HCID 248910Methyl 5-Iodosalicylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Sources & evidence

ORD record
ord-74f76649d4f14d2da80ba9266ac1c634
Source dataset
uspto-grants-2000_09
Patent number
US06114175

Reaction notes

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