4-Hydroxybenzoic Acid → HCID 59592619, compound

HRID 885093Notes

Reaction equation

[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[SH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1>>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([S:11][C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=2)=[CH:13][CH:14]=1

Participants

Reactant 2

HCID 1354-Hydroxybenzoic Acid

HCID 2401474-Mercaptophenol

Product 1

HCID 59592619HCID 59592619, compoundYield 24.4%

Procedure

A PPE (polyphosphate ester) solution (7 mL) was added to a mixture of 4-hydroxybenzoic acid (552 mg, 4 mmol) and 4-mercaptophenol (554 mg, 4.4 mmol). After stirring for 16 h, the solvents were removed by evaporation and the residue was purified by column chromatography (hexane-EtOAc 7:1 to 1:1). 4-Hydroxy-thiobenzoic acid S-(4-hydroxy-phenyl) ester (240 mg, 24%) was obtained as a white solid. MS (ES) m/z: 247.04 (M+1), 167.03, and 122.55. 13C-NMR (DMSO-d6): δ 188.24, 162.85, 158.82, 135.87, 129.59, 127.10, 116.33, 115.72, and 115.34.

Workup

customthe solvents were removed by evaporation
customthe residue was purified by column chromatography (hexane-EtOAc 7:1 to 1:1)

Sources & evidence

ORD record: ord-98f68b71fd7a4c26be532b6748cdda58
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242144B2

Reaction notes

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