2,5-Dihydroxybenzoic acid → Methyl Gentisate

HRID 1598804Notes

Reaction equation

HRID 1598804 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12](C1C=CC(O)=C(C=1)C(OCC)=O)=O>CO>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 34692,5-Dihydroxybenzoic acidHCID 18930679Ethyl 5-formyl-2-hydroxybenzoate

Product 1

HCID 75077Methyl GentisateYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5-Dihydroxybenzoic acid was converted to its methyl ester using catalytic sulfuric acid in methanol following the same protocol as for esterification 2c in 94% yield. mp 86.4°-88.5° C. IR(KBr): cm-1 3346, 1684.

Sources & evidence

ORD record
ord-996d9a42a24d4047850656b9ec242caa
Source dataset
uspto-grants-1998_04
Patent number
US05739163

Reaction notes

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