Protocatechuic Acid → Methyl 3,4-Dihydroxybenzoate

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].Cl.[CH3:13]O>>[CH3:13][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[CH:3]=1

Participants

Reactant 3

HCID 72Protocatechuic Acid

HCID 313Hydrochloric Acid

HCID 887Methanol

Product 1

HCID 287064Methyl 3,4-DihydroxybenzoateYield 86.5%

Procedure

A solution of 3,4-dihydroxy benzoic acid (2.8 g) in methanol (150 ml) was refluxed in presence of concentrated hydrochloric acid (0.5 ml) for 12 hrs. After concentrating under reduced pressure, the residue was dissolved in ethyl acetate (150 ml) and washed with water (50 ml) 10% sodium bicarbonate solution (50 ml), brine solution (50 ml) and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure provided 2.64 g of 3,4-dihydroxybenzoic acid methyl ester. (Yield 86.5%).

Workup

concentrationAfter concentrating under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate (150 ml)
washwashed with water (50 ml) 10% sodium bicarbonate solution (50 ml), brine solution (50 ml)
dry with materialdried over anhydrous magnesium sulfate
customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-10c90eac3e5d4cd08e4480474dc581bb
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745490B2

Reaction notes

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