Benzoic acid, 2-hydroxy-3,5-dinitro- → 2-Nitrophenol

HRID 1828869Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[C:11]([N+]([O-])=O)[CH:10]=[C:6](C(O)=O)[C:5]=1[OH:16])([O-:3])=[O:2].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:6][C:5]=1[OH:16])([O-:3])=[O:2]

Participants

Reactant 3

HCID 11873Benzoic acid, 2-hydroxy-3,5-dinitro-

HCID 12734Diisopropylcarbodiimide

HCID 757711-Hydroxybenzotriazole

Product 1

HCID 69472-Nitrophenol

Procedure

This material was prepared from 3,5-dinitrosalicylic acid (1d) (1 g, 4.4 mmol), HOBt (1 g, 7.4 mmol), DIC (1,3-diisopropylcarodiimide, 1 mL, 6.4 mmol), and an amino macroporous resin (1 g, 0.4 mmol) using a procedure similar to polystyrene resin (PS-2a).

Sources & evidence

ORD record: ord-8c38edad6ed444a5abd7852b488747a5
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060752B2

Reaction notes

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