Protocatechuic Acid → 2-(3,4-dihydroxybenzoyl)oxymethyl-5-hydroxy-4H-pyran-4-one

HRID 259844

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].[OH-].[Na+].[CH:14]1[C:19](=[O:20])[C:18]([OH:21])=[CH:17][O:16][C:15]=1[CH2:22]Cl>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH2:22][C:15]1[O:16][CH:17]=[C:18]([OH:21])[C:19](=[O:20])[CH:14]=1)=[O:6]

Participants

Reactant 3

HCID 72Protocatechuic Acid

HCID 14798Sodium Hydroxide

HCID 82051Chlorokojic acid

Product 1

HCID 224040112-(3,4-dihydroxybenzoyl)oxymethyl-5-hydroxy-4H-pyran-4-oneYield 43.3%

Procedure

By following the procedure of Example 1 by employing 4.22 g(27.4 mmole) of 3,4-dihydroxybenzoic acid, 1.1 g (27.5 mmole) of sodium hydroxide and 4 g(24.9 mmole) of chlorokojic acid, there was obtained 3.0 g(43.3%) of 2-(3,4-dihydroxybenzoyl)oxymethyl-5-hydroxy-4H-pyran-4-one as as a solid.

Sources & evidence

ORD record: ord-bc57c004a36949f6923aeef31c002618
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523421

Linked notes

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