3,5-Bis(trifluoromethyl)phenol → Tetrabutylammonium 3,5-Bis(trifluoromethyl)phenoxide

HRID 1970708Notes

Reaction equation

HRID 1970708 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[CH2:17]([N+:21]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>O.CC(O)C>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[O-:13].[CH2:30]([N+:21]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 2

HCID 676803,5-Bis(trifluoromethyl)phenolHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 86619914Tetrabutylammonium 3,5-Bis(trifluoromethyl)phenoxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a flask were added 1.0 g 3,5-bis(trifluoromethyl)phenol, 1.8 g of a 55-60% solution of tetrabutylammonium hydroxide in water and 10 ml 2-propanol. After heating to 50 C under nitrogen for 1 hour, the solvent was removed and another 10 ml of 2-propanol were added and removed by distillation under reduced pressure. An oil was obtained which crystallized on standing.

Workup

  1. temperatureAfter heating to 50 C under nitrogen for 1 hour
  2. customthe solvent was removed
  3. additionanother 10 ml of 2-propanol were added
  4. customremoved by distillation under reduced pressure
  5. customAn oil was obtained which
  6. customcrystallized

Sources & evidence

ORD record
ord-fbc09f0560be4b0481ba6f6099dbd4bf
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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