M-Cresol → 3-Methyl-2-nitrophenol

HRID 258639

Reaction equation

[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:8].S(=O)(=O)(O)O.[N+:14]([O-])([OH:16])=[O:15]>>[CH3:8][C:2]1[C:1]([N+:14]([O-:16])=[O:15])=[C:6]([OH:7])[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 342M-Cresol

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

Product 1

HCID 210263-Methyl-2-nitrophenol

Procedure

Furthermore, there is disclosed in Journal of Chemical Society, 1277 (1923) that m-cresol is sulfonated with a fuming sulfuric acid and then the resulting sulfonated m-cresol is nitrated with a mixed acid (nitric acid plus sulfuric acid), but by this method 3-methyl-2-nitrophenol is obtained as a main product and only a small amount of 5-methyl-2-nitrophenol is obtained as a by-product, the total yield being very poor for the reason as mentioned above.

Sources & evidence

ORD record: ord-357f60c16d7c4bdb9522970e7a591d01
Source dataset: uspto-grants-1977_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04034050

Linked notes

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