Nitric Acid → 2-Nitro-5-(trifluoromethyl)phenol

HRID 660814Notes

Reaction equation

HRID 660814 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[N+:12]([O-])([OH:14])=[O:13]>CC(O)=O>[N+:12]([C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][C:5]=1[OH:9])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 73763-(Trifluoromethyl)phenol

Product 1

HCID 140916902-Nitro-5-(trifluoromethyl)phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 3-trifluoromethylphenol (3.0 mL, 25 mmol) in HOAc (10 mL) is added dropwise to a solution of 65% nitric acid (2.0 mL, 278 mmol) in HOAc (10 mL) at 0° C. The mixture is warmed to 40° C. and when the reaction is complete it is cooled to RT and partitioned between water and EtOAc. The organic layer is concentrated and the residue is chromatographed using 10% EtOAc/hexane as eluent to afford the title compound as a yellow oil: (M−1)−=206.

Workup

  1. temperatureis cooled to RT
  2. custompartitioned between water and EtOAc
  3. concentrationThe organic layer is concentrated
  4. customthe residue is chromatographed

Sources & evidence

ORD record
ord-a37f1e374e564f7582afc70f40acfce0
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…