Nitric Acid → 2-Hydroxy-3-nitrobiphenyl

HRID 746255Notes

Reaction equation

HRID 746255 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[OH:1][C:2]1[C:7]([N+:14]([O-:16])=[O:15])=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 7017(1,1'-Biphenyl)-2-ol

Product 1

HCID 1607452-Hydroxy-3-nitrobiphenyl

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In step (1) of Reaction Scheme 1, a 2-hydroxybiphenyl of Formula II is nitrated using nitric acid in the presence of acetic acid to provide a 2-hydroxy-3-nitrobiphenyl of Formula III. A preferred method of carrying out this reaction is as follows. The biphenyl of Formula II is dissolved in glacial acetic acid at a temperature of 15° to 20° C. Concentrated nitric acid is then added thereto and the resulting mixture is stirred for a short period of time (usually less than about one hour). Thereafter the mixture is diluted with an equal volume of water. The 2-hydroxy-3-nitrobiphenyl of Formula III is separated from the mixture, usually as an oil, and is triturated with hot hexane and purified by chromatography. As an alternative to conducting step (1), known 2-hydroxy-3-nitrobiphenyls may be employed directly in step (2) below.

Workup

  1. customIn step (1) of Reaction Scheme 1

Sources & evidence

ORD record
ord-1cc6979e2a5147f089ecfc1f59070963
Source dataset
uspto-grants-1986_07
Patent number
US04603199

Reaction notes

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