Toluene → 2-(3-Hydroxyphenoxy)-6-(trifluoromethyl)benzonitrile

HRID 354094Notes

Reaction equation

HRID 354094 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[OH-].[K+].Cl[C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:13]=1[C:14]#[N:15].C1(C)C=CC=CC=1>CN1CCCC1=O.O>[C:14]([C:13]1[C:16]([C:20]([F:21])([F:22])[F:23])=[CH:17][CH:18]=[CH:19][C:12]=1[O:2][C:1]1[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)#[N:15]

Participants

7

Reactant 4

HCID 1140TolueneHCID 5054ResorcinolHCID 14797Potassium HydroxideHCID 108674572-chloro-6-(trifluoromethyl)benzonitrile

Product 1

HCID 129718822-(3-Hydroxyphenoxy)-6-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
62.5 °C

Procedure

Resorcinol [44.0 g (0.4 mol)] is partly dissolved in 170 ml of N-methylpyrrolidone, and potassium hydroxide [min. 85% pure; 34.5 g (0.52 mol)] and then 2-chloro-6-(trifluoromethyl)benzonitrile [20.5 g (0.1 mol)] are added. The mixture is stirred at 60-65° C. for 2.5 h. After addition of 300 ml of toluene and 400 ml of water, the aqueous phase is separated off and extracted once more with 300 ml of toluene. The combined organic phases are dried over MgSO4 and, after filtration, concentrated. Digestion of the oily residue with 150 ml of water, filtration and drying affords pale brownish crystals.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted once more with 300 ml of toluene
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. filtrationafter filtration
  5. concentrationconcentrated
  6. filtrationDigestion of the oily residue with 150 ml of water, filtration
  7. customdrying
  8. customaffords pale brownish crystals

Sources & evidence

ORD record
ord-2945f618b9dd40b1844272a909f19fa1
Source dataset
uspto-grants-2004_06
Patent number
US06756409B2

Reaction notes

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