Guaiacol → 2-Methoxy-3-nitrophenol

HRID 1014936Notes

Reaction equation

HRID 1014936 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13]>C(Cl)Cl>[CH3:5][O:6][C:7]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13]

Participants

4

Reactant 2

HCID 460GuaiacolHCID 944Nitric Acid

Product 1

HCID 136813592-Methoxy-3-nitrophenolYield 29,562.199%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fuming HNO3 (0.34 mL, 0.008 mmol) was carefully added to a mixture of 2-methoxyphenol (0.886 mL, 0.008 mmol) in anhydrous DCM (10 mL) at −20° C. After stirring for 2 h at RT, the mixture was concentrated under vacuum. Chromatography (10-30% EtOAc/hexanes) provided 9A12 (400 mg, 29%) and 2-methoxy-3-nitrophenol (400 mg, 29%).

Workup

  1. concentrationthe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-8dcb3ee8c19c487b965757c8f6a189e3
Source dataset
uspto-grants-2011_07
Patent number
US07985748B2

Reaction notes

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